Organic electroluminescent materials and devices

ABSTRACT

An OLED including an organic layer that contains metal complex compounds that are useful as a phosphorescent emitter is disclosed. The metal complex compounds include ligands that incorporate fluorinated side chains and has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring, In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. patent application Ser. No.15/177,906, filed on Jun. 9, 2016, which is a continuation of U.S.patent application Ser. No. 14/509,274, filed on Oct. 8, 2014, nowissued as U.S. Pat. No. 9,397,302, issued on Jul. 19, 2016.

FIELD OF THE INVENTION

The present invention relates to novel ligands for metal complexes foruse as emitters and devices, such as organic light emitting diodes,including the same.

BACKGROUND

Opto-electronic devices that make use of organic materials are becomingincreasingly desirable for a number of reasons. Many of the materialsused to make such devices are relatively inexpensive, so organicopto-electronic devices have the potential for cost advantages overinorganic devices. In addition, the inherent properties of organicmaterials, such as their flexibility, may make them well suited forparticular applications such as fabrication on a flexible substrate.Examples of organic opto-electronic devices include organic lightemitting devices (OLEDs), organic phototransistors, organic photovoltaiccells, and organic photodetectors. For OLEDs, the organic materials mayhave performance advantages over conventional materials. For example,the wavelength at which an organic emissive layer emits light maygenerally be readily tuned with appropriate dopants.

OLEDs make use of thin organic films that emit light when voltage isapplied across the device. OLEDs are becoming an increasinglyinteresting technology for use in applications such as flat paneldisplays, illumination, and backlighting. Several OLED materials andconfigurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and5,707,745, which are incorporated herein by reference in their entirety.

One application for phosphorescent emissive molecules is a full colordisplay. Industry standards for such a display call for pixels adaptedto emit particular colors, referred to as “saturated” colors. Inparticular, these standards call for saturated red, green, and bluepixels. Color may be measured using CIE coordinates, which are wellknown to the art.

One example of a green emissive molecule is tris(2-phenylpyridine)iridium, denoted Ir(ppy)₃, which has the following structure:

In this, and later figures herein, we depict the dative bond fromnitrogen to metal (here, Ir) as a straight line.

As used herein, the term “organic” includes polymeric materials as wellas small molecule organic materials that may be used to fabricateorganic opto-electronic devices. “Small molecule” refers to any organicmaterial that is not a polymer, and “small molecules” may actually bequite large. Small molecules may include repeat units in somecircumstances. For example, using a long chain alkyl group as asubstituent does not remove a molecule from the “small molecule” class.Small molecules may also be incorporated into polymers, for example as apendent group on a polymer backbone or as a part of the backbone. Smallmolecules may also serve as the core moiety of a dendrimer, whichconsists of a series of chemical shells built on the core moiety. Thecore moiety of a dendrimer may be a fluorescent or phosphorescent smallmolecule emitter. A dendrimer may be a “small molecule,” and it isbelieved that all dendrimers currently used in the field of OLEDs aresmall molecules.

As used herein, “top” means furthest away from the substrate, while“bottom” means closest to the substrate. Where a first layer isdescribed as “disposed over” a second layer, the first layer is disposedfurther away from substrate. There may be other layers between the firstand second layer, unless it is specified that the first layer is “incontact with” the second layer. For example, a cathode may be describedas “disposed over” an anode, even though there are various organiclayers in between.

As used herein, “solution processible” means capable of being dissolved,dispersed, or transported in and/or deposited from a liquid medium,either in solution or suspension form.

A ligand may be referred to as “photoactive” when it is believed thatthe ligand directly contributes to the photoactive properties of anemissive material. A ligand may be referred to as “ancillary” when it isbelieved that the ligand does not contribute to the photoactiveproperties of an emissive material, although an ancillary ligand mayalter the properties of a photoactive ligand.

As used herein, and as would be generally understood by one skilled inthe art, a first “Highest Occupied Molecular Orbital” (HOMO) or “LowestUnoccupied Molecular Orbital” (LUMO) energy level is “greater than” or“higher than” a second HOMO or LUMO energy level if the first energylevel is closer to the vacuum energy level. Since ionization potentials(IP) are measured as a negative energy relative to a vacuum level, ahigher HOMO energy level corresponds to an IP having a smaller absolutevalue (an IP that is less negative). Similarly, a higher LUMO energylevel corresponds to an electron affinity (EA) having a smaller absolutevalue (an EA that is less negative). On a conventional energy leveldiagram, with the vacuum level at the top, the LUMO energy level of amaterial is higher than the HOMO energy level of the same material. A“higher” HOMO or LUMO energy level appears closer to the top of such adiagram than a “lower” HOMO or LUMO energy level.

As used herein, and as would be generally understood by one skilled inthe art, a first work function is “greater than” or “higher than” asecond work function if the first work function has a higher absolutevalue. Because work functions are generally measured as negative numbersrelative to vacuum level, this means that a “higher” work function ismore negative. On a conventional energy level diagram, with the vacuumlevel at the top, a “higher” work function is illustrated as furtheraway from the vacuum level in the downward direction. Thus, thedefinitions of HOMO and LUMO energy levels follow a different conventionthan work functions.

More details on OLEDs, and the definitions described above, can be foundin U.S. Pat. No. 7,279,704, which is incorporated herein by reference inits entirety.

SUMMARY OF THE INVENTION

This invention discloses novel ligands for metal complexes that areuseful as a phosponrescent emitter in organic light emitting device.Applicant believes that incorporation of the new side chains on theligands allow the fine tuning of emission color of the metal complexwhile maintaining good device efficiency and device lifetime.

According to an embodiment, a composition comprising a novel compound isdisclosed, wherein the compound is capable of functioning as aphosphorescent emitter in an organic light emitting device at roomtemperature. The compound has at least one aromatic ring and at leastone substituent R, wherein each of the at least one R is independentlyselected from the group consisting of partially fluorinated alkyl,partially fluorinated cycloalkyl, and combinations thereof, wherein eachof the at least one R is directly bonded to one of the aromatic rings,wherein in each of the at least one R, C having an F attached thereto isseparated by at least one carbon atom from the aromatic ring.

According to another embodiment, a first device comprising a firstorganic light emitting device is also provided. The first organic lightemitting device can include an anode, a cathode, and an organic layer,disposed between the anode and the cathode. The organic layer caninclude the compound having at least one aromatic ring and at least onesubstituent R, wherein each of the at least one R is independentlyselected from the group consisting of partially fluorinated alkyl,partially fluorinated cycloalkyl, and combinations thereof; wherein eachof the at least one R is directly bonded to one of the aromatic rings,wherein in each of the at least one R, C having an F attached thereto isseparated by at least one carbon atom from the aromatic ring. The firstdevice can be a consumer product, an organic light-emitting device,and/or a lighting panel.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows an organic light emitting device.

FIG. 2 shows an inverted organic light emitting device that does nothave a separate electron transport layer.

DETAILED DESCRIPTION

Generally, an OLED comprises at least one organic layer disposed betweenand electrically connected to an anode and a cathode. When a current isapplied, the anode injects holes and the cathode injects electrons intothe organic layer(s). The injected holes and electrons each migratetoward the oppositely charged electrode. When an electron and holelocalize on the same molecule, an “exciton,” which is a localizedelectron-hole pair having an excited energy state, is formed. Light isemitted when the exciton relaxes via a photoemissive mechanism. In somecases, the exciton may be localized on an excimer or an exciplex.Non-radiative mechanisms, such as thermal relaxation, may also occur,but are generally considered undesirable.

The initial OLEDs used emissive molecules that emitted light from theirsinglet states (“fluorescence”) as disclosed, for example, in U.S. Pat.No. 4,769,292, which is incorporated by reference in its entirety.Fluorescent emission generally occurs in a time frame of less than 10nanoseconds.

More recently, OLEDs having emissive materials that emit light fromtriplet states (“phosphorescence”) have been demonstrated. Baldo et al.,“Highly Efficient Phosphorescent Emission from OrganicElectroluminescent Devices,” Nature, vol. 395, 151-154, 1998;(“Baldo-I”) and Baldo et al., “Very high-efficiency green organiclight-emitting devices based on electrophosphorescence,” Appl. Phys.Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”), which are incorporatedby reference in their entireties. Phosphorescence is described in moredetail in U.S. Pat. No. 7,279,704 at cols. 5-6, which are incorporatedby reference.

FIG. 1 shows an organic light emitting device 100. The figures are notnecessarily drawn to scale. Device 100 may include a substrate 110, ananode 115, a hole injection layer 120, a hole transport layer 125, anelectron blocking layer 130, an emissive layer 135, a hole blockinglayer 140, an electron transport layer 145, an electron injection layer150, a protective layer 155, a cathode 160, and a barrier layer 170.Cathode 160 is a compound cathode having a first conductive layer 162and a second conductive layer 164. Device 100 may be fabricated bydepositing the layers described, in order. The properties and functionsof these various layers, as well as example materials, are described inmore detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which areincorporated by reference.

More examples for each of these layers are available. For example, aflexible and transparent substrate-anode combination is disclosed inU.S. Pat. No. 5,844,363, which is incorporated by reference in itsentirety. An example of a p-doped hole transport layer is m-MTDATA dopedwith F₄-TCNQ at a molar ratio of 50:1, as disclosed in U.S. PatentApplication Publication No. 2003/0230980, which is incorporated byreference in its entirety. Examples of emissive and host materials aredisclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which isincorporated by reference in its entirety. An example of an n-dopedelectron transport layer is BPhen doped with Li at a molar ratio of 1:1,as disclosed in U.S. Patent Application Publication No. 2003/0230980,which is incorporated by reference in its entirety. U.S. Pat. Nos.5,703,436 and 5,707,745, which are incorporated by reference in theirentireties, disclose examples of cathodes including compound cathodeshaving a thin layer of metal such as Mg:Ag with an overlyingtransparent, electrically-conductive, sputter-deposited ITO layer. Thetheory and use of blocking layers is described in more detail in U.S.Pat. No. 6,097,147 and U.S. Patent Application Publication No.2003/0230980, which are incorporated by reference in their entireties.Examples of injection layers are provided in U.S. Patent ApplicationPublication No. 2004/0174116, which is incorporated by reference in itsentirety. A description of protective layers may be found in U.S. PatentApplication Publication No. 2004/0174116, which is incorporated byreference in its entirety.

FIG. 2 shows an inverted OLED 200. The device includes a substrate 210,a cathode 215, an emissive layer 220, a hole transport layer 225, and ananode 230. Device 200 may be fabricated by depositing the layersdescribed, in order. Because the most common OLED configuration has acathode disposed over the anode, and device 200 has cathode 215 disposedunder anode 230, device 200 may be referred to as an “inverted” OLED.Materials similar to those described with respect to device 100 may beused in the corresponding layers of device 200. FIG. 2 provides oneexample of how some layers may be omitted from the structure of device100.

The simple layered structure illustrated in FIGS. 1 and 2 is provided byway of non-limiting example, and it is understood that embodiments ofthe invention may be used in connection with a wide variety of otherstructures. The specific materials and structures described areexemplary in nature, and other materials and structures may be used.Functional OLEDs may be achieved by combining the various layersdescribed in different ways, or layers may be omitted entirely, based ondesign, performance, and cost factors. Other layers not specificallydescribed may also be included. Materials other than those specificallydescribed may be used. Although many of the examples provided hereindescribe various layers as comprising a single material, it isunderstood that combinations of materials, such as a mixture of host anddopant, or more generally a mixture, may be used. Also, the layers mayhave various sublayers. The names given to the various layers herein arenot intended to be strictly limiting. For example, in device 200, holetransport layer 225 transports holes and injects holes into emissivelayer 220, and may be described as a hole transport layer or a holeinjection layer. In one embodiment, an OLED may be described as havingan “organic layer” disposed between a cathode and an anode. This organiclayer may comprise a single layer, or may further comprise multiplelayers of different organic materials as described, for example, withrespect to FIGS. 1 and 2.

Structures and materials not specifically described may also be used,such as OLEDs comprised of polymeric materials (PLEDs) such as disclosedin U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated byreference in its entirety. By way of further example, OLEDs having asingle organic layer may be used. OLEDs may be stacked, for example asdescribed in U.S. Pat. No. 5,707,745 to Forrest et al, which isincorporated by reference in its entirety. The OLED structure maydeviate from the simple layered structure illustrated in FIGS. 1 and 2.For example, the substrate may include an angled reflective surface toimprove out-coupling, such as a mesa structure as described in U.S. Pat.No. 6,091,195 to Forrest et al., and/or a pit structure as described inU.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated byreference in their entireties.

Unless otherwise specified, any of the layers of the various embodimentsmay be deposited by any suitable method. For the organic layers,preferred methods include thermal evaporation, ink-jet, such asdescribed in U.S. Pat. Nos. 6,013,982 and 6,087,196, which areincorporated by reference in their entireties, organic vapor phasedeposition (OVPD), such as described in U.S. Pat. No. 6,337,102 toForrest et al., which is incorporated by reference in its entirety, anddeposition by organic vapor jet printing (OVJP), such as described inU.S. Pat. No. 7,431,968, which is incorporated by reference in itsentirety. Other suitable deposition methods include spin coating andother solution based processes. Solution based processes are preferablycarried out in nitrogen or an inert atmosphere. For the other layers,preferred methods include thermal evaporation. Preferred patterningmethods include deposition through a mask, cold welding such asdescribed in U.S. Pat. Nos. 6,294,398 and 6,468,819, which areincorporated by reference in their entireties, and patterning associatedwith some of the deposition methods such as ink-jet and OVJD. Othermethods may also be used. The materials to be deposited may be modifiedto make them compatible with a particular deposition method. Forexample, substituents such as alkyl and aryl groups, branched orunbranched, and preferably containing at least 3 carbons, may be used insmall molecules to enhance their ability to undergo solution processing.Substituents having 20 carbons or more may be used, and 3-20 carbons isa preferred range. Materials with asymmetric structures may have bettersolution processibility than those having symmetric structures, becauseasymmetric materials may have a lower tendency to recrystallize.Dendrimer substituents may be used to enhance the ability of smallmolecules to undergo solution processing.

Devices fabricated in accordance with embodiments of the presentinvention may further optionally comprise a barrier layer. One purposeof the barrier layer is to protect the electrodes and organic layersfrom damaging exposure to harmful species in the environment includingmoisture, vapor and/or gases, etc. The barrier layer may be depositedover, under or next to a substrate, an electrode, or over any otherparts of a device including an edge. The barrier layer may comprise asingle layer, or multiple layers. The barrier layer may be formed byvarious known chemical vapor deposition techniques and may includecompositions having a single phase as well as compositions havingmultiple phases. Any suitable material or combination of materials maybe used for the barrier layer. The barrier layer may incorporate aninorganic or an organic compound or both. The preferred barrier layercomprises a mixture of a polymeric material and a non-polymeric materialas described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos.PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporatedby reference in their entireties. To be considered a “mixture”, theaforesaid polymeric and non-polymeric materials comprising the barrierlayer should be deposited under the same reaction conditions and/or atthe same time. The weight ratio of polymeric to non-polymeric materialmay be in the range of 95:5 to 5:95. The polymeric material and thenon-polymeric material may be created from the same precursor material.In one example, the mixture of a polymeric material and a non-polymericmaterial consists essentially of polymeric silicon and inorganicsilicon.

Devices fabricated in accordance with embodiments of the invention canbe incorporated into a wide variety of electronic component modules (orunits) that can be incorporated into a variety of electronic products orintermediate components. Examples of such electronic products orintermediate components include display screens, lighting devices suchas discrete light source devices or lighting panels, etc. that can beutilized by the end-user product manufacturers. Such electroniccomponent modules can optionally include the driving electronics and/orpower source(s). Devices fabricated in accordance with embodiments ofthe invention can be incorporated into a wide variety of consumerproducts that have one or more of the electronic component modules (orunits) incorporated therein. Such consumer products would include anykind of products that include one or more light source(s) and/or one ormore of some type of visual displays. Some examples of such consumerproducts include flat panel displays, computer monitors, medicalmonitors, televisions, billboards, lights for interior or exteriorillumination and/or signaling, heads-up displays, fully or partiallytransparent displays, flexible displays, laser printers, telephones,cell phones, tablets, phablets, personal digital assistants (PDAs),laptop computers, digital cameras, camcorders, viewfinders,micro-displays, 3-D displays, vehicles, a large area wall, theater orstadium screen, or a sign. Various control mechanisms may be used tocontrol devices fabricated in accordance with the present invention,including passive matrix and active matrix. Many of the devices areintended for use in a temperature range comfortable to humans, such as18 degrees C. to 30 degrees C., and more preferably at room temperature(20-25 degrees C.), but could be used outside this temperature range,for example, from −40 degree C. to +80 degree C.

The materials and structures described herein may have applications indevices other than OLEDs. For example, other optoelectronic devices suchas organic solar cells and organic photodetectors may employ thematerials and structures. More generally, organic devices, such asorganic transistors, may employ the materials and structures.

The term “halo,” “halide,” or “halogen” as used herein includesfluorine, chlorine, bromine, and iodine.

The term “alkyl” as used herein contemplates both straight and branchedchain alkyl radicals. Preferred alkyl groups are those containing fromone to fifteen carbon atoms and includes methyl, ethyl, propyl,isopropyl, butyl, isobutyl, tert-butyl, and the like. Additionally, thealkyl group may be optionally substituted.

The term “cycloalkyl” as used herein contemplates cyclic alkyl radicals.Preferred cycloalkyl groups are those containing 3 to 7 carbon atoms andincludes cyclopropyl, cyclopentyl, cyclohexyl, and the like.Additionally, the cycloalkyl group may be optionally substituted.

The term “alkenyl” as used herein contemplates both straight andbranched chain alkene radicals. Preferred alkenyl groups are thosecontaining two to fifteen carbon atoms. Additionally, the alkenyl groupmay be optionally substituted.

The term “alkynyl” as used herein contemplates both straight andbranched chain alkyne radicals. Preferred alkynyl groups are thosecontaining two to fifteen carbon atoms. Additionally, the alkynyl groupmay be optionally substituted.

The terms “aralkyl” or “arylalkyl” as used herein are usedinterchangeably and contemplate an alkyl group that has as a substituentan aromatic group. Additionally, the aralkyl group may be optionallysubstituted.

The term “heterocyclic group” as used herein contemplates aromatic andnon-aromatic cyclic radicals. Hetero-aromatic cyclic radicals also meansheteroaryl. Preferred hetero-non-aromatic cyclic groups are thosecontaining 3 or 7 ring atoms which includes at least one hetero atom,and includes cyclic amines such as morpholino, piperdino, pyrrolidino,and the like, and cyclic ethers, such as tetrahydrofuran,tetrahydropyran, and the like. Additionally, the heterocyclic group maybe optionally substituted.

The term “aryl” or “aromatic group” as used herein contemplatessingle-ring groups and polycyclic ring systems. The polycyclic rings mayhave two or more rings in which two carbons are common to two adjoiningrings (the rings are “fused”) wherein at least one of the rings isaromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl,heterocycles, and/or heteroaryls. Additionally, the aryl group may beoptionally substituted.

The term “heteroaryl” as used herein contemplates single-ringhetero-aromatic groups that may include from one to three heteroatoms,for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole,triazole, pyrazole, pyridine, pyrazine and pyrimidine, and the like. Theterm heteroaryl also includes polycyclic hetero-aromatic systems havingtwo or more rings in which two atoms are common to two adjoining rings(the rings are “fused”) wherein at least one of the rings is aheteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls,aryl, heterocycles, and/or heteroaryls. Additionally, the heteroarylgroup may be optionally substituted.

The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclic group,aryl, and heteroaryl may be optionally substituted with one or moresubstituents selected from the group consisting of hydrogen, deuterium,halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy,amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl,alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether,ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, andcombinations thereof.

As used herein, “substituted” indicates that a substituent other than His bonded to the relevant position, such as carbon. Thus, for example,where R¹ is mono-substituted, then one R¹ must be other than H.Similarly, where R¹ is di-substituted, then two of R¹ must be other thanH. Similarly, where R¹ is unsubstituted, R¹ is hydrogen for allavailable positions.

The “aza” designation in the fragments described herein, i.e.aza-dibenzofuran, aza-dibenzothiophene, etc. means that one or more ofthe C—H groups in the respective fragment can be replaced by a nitrogenatom, for example, and without any limitation, azatriphenyleneencompasses both dibenzo[fh]quinoxaline and dibenzo[fh]quinoline. One ofordinary skill in the art can readily envision other nitrogen analogs ofthe aza-derivatives described above, and all such analogs are intendedto be encompassed by the terms as set forth herein.

It is to be understood that when a molecular fragment is described asbeing a substituent or otherwise attached to another moiety, its namemay be written as if it were a fragment (e.g. phenyl, phenylene,naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g.benzene, naphthalene, dibenzofuran). As used herein, these differentways of designating a substituent or attached fragment are considered tobe equivalent.

According to an embodiment, a composition comprising a novel firstcompound is disclosed, wherein the first compound is capable offunctioning as a phosphorescent emitter in an organic light emittingdevice at room temperature. The first compound has at least one aromaticring and at least one substituent R, wherein each of the at least onesubstituent R is independently selected from the group consisting ofpartially fluorinated alkyl, partially fluorinated cycloalkyl, andcombinations thereof, wherein each of the at least one substituent R isdirectly bonded to one of the aromatic rings, and wherein in each of theat least one substituent R, C having an F attached thereto is separatedby at least one carbon atom from the aromatic ring.

Each of the at least one substituent R being directly bonded to one ofthe aromatic rings means that each R can be bonded to different aromaticrings or some of the Rs can be bonded to the same aromatic ring.Partially fluorinated group means that not all of the carbon-hydrogenbonds in a group have been replaced by carbon-fluorine bonds, in otherwords, there is at least one carbon-hydrogen bond remaining in thatgroup.

In one embodiment, the first compound is capable of emitting light froma triplet excited state to a ground singlet state at room temperature.

In one embodiment, the first compound is a metal coordination complexhaving a metal-carbon bond. The metal can be selected from the groupconsisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu. In one preferredembodiment, the metal is Ir. In another preferred embodiment, the metalis Pt.

In one embodiment of the first compound, C having an F attached theretois separated by at least two carbon atoms from the aromatic ring. Inanother embodiment, C having an F attached thereto is separated by atleast three carbon atoms from the aromatic ring.

In one embodiment of the first compound, each of the at least onesubstituent R contains at least one CF₃ group. In a preferredembodiment, each of the at least one substituent R contains only CF₃group and no CF or CF₂ groups. In another embodiment, none of the atleast one substituent R contain any CF₃ groups.

In one embodiment, the first compound does not have any F atoms otherthan those in the at least one substituent R.

In one embodiment of the first compound, the aromatic ring comprisesLUMO electron density of the first compound.

In one embodiment of the first compound, m in the formulaC_(n)H_(2n+1−m)F_(m) and C_(q)H_(2q−1−m)F_(m) is not a multiple of 3. Inanother embodiment, m is a multiple of 3.

According to an aspect of the present disclosure, the first compound asdefined above has the formula of M(L¹)_(x)(L²)_(y)(L³)_(z); wherein L¹,L², and L³ can be the same or different;

-   -   wherein x is 1, 2, or 3;    -   wherein y is 0, 1, or 2;    -   wherein z is 0, 1, or 2;    -   wherein x+y+z is the oxidation state of the metal M;    -   wherein L¹, L², and L³ are each independently selected from the        group consisting of:

-   -   wherein R_(a), R_(b), R_(c) and R_(d) independently represent        mono, di, tri, or tetra substitution, or no substitution;    -   wherein R_(a), R_(b), R_(c) and R_(d) are independently selected        from the group consisting of hydrogen, deuterium, halide, alkyl,        cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino,        silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl,        heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile,        isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and        combinations thereof;    -   wherein two adjacent substituents of R_(a), R_(b), R_(c), and        R_(d) are optionally joined to form a ring or form a        multidentate ligand; and wherein at least one of R_(a), R_(b),        R_(c), and R_(d) includes at least one R.

In one embodiment of the first compound as defined above, M is Ir andthe first compound has the formula of Ir(L¹)₂(L²). In the first compoundhaving the formula of Ir(L¹)₂(L²), L¹ has the formula selected from thegroup consisting of:

and L² has the formula:

wherein R_(a), R_(b), and R_(c) independently represent mono, di, tri,or tetra substitution, or no substitution;

wherein R_(a), R_(b), and R_(c) are independently selected from thegroup consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl,heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl,cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl,carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl,sulfonyl, phosphino, and combinations thereof;

wherein two adjacent substituents of R_(a), R_(b), and R_(c) areoptionally joined to form a ring or form a multidentate ligand; andwherein at least one of R_(a), R_(b), and R_(c) includes at least one R.

In another embodiment of the first compound as defined above, M is Irand the first compound has the formula of Ir(L¹)₂(L²) where L¹ has theformula selected from the group consisting of:

L² has the formula:

wherein R_(a) and R_(b) are as defined above and R_(e), R_(f), R_(h),and R_(i) are independently selected from group consisting of alkyl,cycloalkyl, aryl, and heteroaryl;

wherein at least one of R_(e), R_(f), R_(h), and R_(i) has at least twocarbon atoms;

wherein R_(g) is selected from group consisting of hydrogen, deuterium,halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy,amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl,heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile,isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinationsthereof; and wherein at least one of R_(a) and R_(b) includes at leastone R.

In another embodiment of the first compound having the formula ofIr(L¹)₂(L²) as defined above, L¹ and L² are different and each areindependently selected from the group consisting of:

wherein at least one of R_(a) and R_(b) includes at least one R.

In another embodiment of the first compound having the formula ofIr(L¹)₂(L²), L¹ and L² are each independently selected from the groupconsisting of:

wherein at least one of R_(a), R_(b), and R_(c) includes at least one R.

In the embodiment where the first compound has a structure according tothe formula M(L¹)_(x)(L²)_(y)(L³)_(z) defined above, the compound canhave the formula of Pt(L¹)₂ or Pt(L¹)(L²). In the compound having theformula of Pt(L¹)₂, L¹ can be connected to the other L¹. In the compoundhaving the formula Pt(L¹)(L²), L¹ can be connected to L² to form atetradentate ligand. In one embodiment, at least one of R_(a), R_(b),R_(c), and R_(d) includes an alkyl or cycloalkyl group that includes CD,CD₂, or CD₃, wherein D is deuterium.

According to another aspect of the present disclosure, in the firstcompound having the formula of M(L¹)_(x)(L²)_(y)(L³)_(z); L¹, L², and L³can be the same or different;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

wherein x+y+z is the oxidation state of the metal M;

wherein L¹, L², and L³ are each independently selected from the groupconsisting of

wherein in L_(A1), R = R^(A1), in L_(A2), R = R^(A2), in L_(A3), R =R^(A3), in L_(A4), R = R^(A4), in L_(A5), R = R^(A5), in L_(A6), R =R^(A6), in L_(A7), R = R^(A7), in L_(A8), R = R^(A8), in L_(A9), R =R^(A9), in L_(A10), R = R^(A10), in L_(A11), R = R^(A11), in L_(A12), R= R^(A12), in L_(A13), R = R^(A13), in L_(A14), R = R^(A14), in L_(A15),R = R^(A15), in L_(A16), R = R^(A16), in L_(A17), R = R^(A17), inL_(A18), R = R^(A18), in L_(A19), R = R^(A19), in L_(A20), R = R^(A20),in L_(A21), R = R^(A21), in L_(A22), R = R^(A22), in L_(A23), R =R^(A23), in L_(A24), R = R^(A24), in L_(A25), R = R^(A25), in L_(A26), R= R^(A26), in L_(A27), R = R^(A27), in L_(A28), R = R^(A28), in L_(A29),R = R^(A29), in L_(A30), R = R^(A30), in L_(A31), R = R^(A31), inL_(A32), R = R^(A32), in L_(A33), R = R^(A33), in L_(A34), R = R^(A34),in L_(A35), R = R^(A35), in L_(A36), R = R^(A36), in L_(A37), R =R^(A37), in L_(A38), R = R^(A38), in L_(A39), R = R^(A39), in L_(A40), R= R^(A40), and in L_(A41), R = R^(A41);

wherein in L_(A42), R = R^(A1), in L_(A43), R = R^(A2), in L_(A44), R =R^(A3), in L_(A45), R = R^(A4), in L_(A46), R = R^(A5), in L_(A47), R =R^(A6), in L_(A48), R = R^(A7), in L_(A49), R = R^(A8), in L_(A50), R =R^(A9), in L_(A51), R = R^(A10), in L_(A52), R = R^(A11), in L_(A53), R= R^(A12), in L_(A54), R = R^(A13), in L_(A55), R = R^(A14), in L_(A56),R = R^(A15), in L_(A57), R = R^(A16), in L_(A58), R = R^(A17), inL_(A59), R = R^(A18), in L_(A60), R = R^(A19), in L_(A61), R = R^(A20),in L_(A62), R = R^(A21), in L_(A63), R = R^(A22), in L_(A64), R =R^(A23), in L_(A65), R = R^(A24), in L_(A66), R = R^(A25), in L_(A67), R= R^(A26), in L_(A68), R = R^(A27), in L_(A69), R = R^(A28), in L_(A70),R = R^(A29), in L_(A71), R = R^(A30), in L_(A72), R = R^(A31), inL_(A73), R = R^(A32), in L_(A74), R = R^(A33), in L_(A75), R = R^(A34),in L_(A76), R = R^(A35), in L_(A77), R = R^(A36), in L_(A78), R =R^(A37), in L_(A79), R = R^(A38), in L_(A80), R = R^(A39), in L_(A81), R= R^(A40), and in L_(A82), R = R^(A41);

wherein in L_(A83), R = R^(A1), in L_(A84), R = R^(A2), in L_(A85), R =R^(A3), in L_(A86), R = R^(A4), in L_(A87), R = R^(A5), in L_(A88), R =R^(A6), in L_(A89), R = R^(A7), in L_(A90), R = R^(A8), in L_(A91), R =R^(A9), in L_(A92), R = R^(A10), in L_(A93), R = R^(A11), in L_(A94), R= R^(A12), in L_(A95), R = R^(A13), in L_(A96), R = R^(A14), in L_(A97),R = R^(A15), in L_(A98), R = R^(A16), in L_(A99), R = R^(A17), inL_(A100), R = R^(A18), in L_(A101), R = R^(A19), in L_(A102), R =R^(A20), in L_(A103), R = R^(A21), in L_(A104), R = R^(A22), inL_(A105), R = R^(A23), in L_(A106), R = R^(A24), in L_(A107), R =R^(A25), in L_(A108), R = R^(A26), in L_(A109), R = R^(A27), inL_(A110), R = R^(A28), in L_(A111), R = R^(A29), in L_(A112), R =R^(A30), in L_(A113), R = R^(A31), in L_(A114), R = R^(A32), inL_(A115), R = R^(A33), in L_(A116), R = R^(A34), in L_(A117), R =R^(A35), in L_(A118), R = R^(A36), in L_(A119), R = R^(A37), inL_(A120), R = R^(A38), in L_(A121), R = R^(A39), in L_(A122), R =R^(A40), and in L_(A123), R = R^(A41);

wherein in L_(A124), R = R^(A1), in L_(A125), R = R^(A2), in L_(A126), R= R^(A3), in L_(A127), R = R^(A4), in L_(A128), R = R^(A5), in L_(A129),R = R^(A6), in L_(A130), R = R^(A7), in L_(A131), R = R^(A8), inL_(A132), R = R^(A9), in L_(A133), R = R^(A10), in L_(A134), R =R^(A11), in L_(A135), R = R^(A12), in L_(A136), R = R^(A13), inL_(A137), R = R^(A14), in L_(A138), R = R^(A15), in L_(A139), R =R^(A16), in L_(A140), R = R^(A17), in L_(A141), R = R^(A18), inL_(A142), R = R^(A19), in L_(A143), R = R^(A20), in L_(A144), R =R^(A21), in L_(A145), R = R^(A22), in L_(A146), R = R^(A23), inL_(A147), R = R^(A24), in L_(A148), R = R^(A25), in L_(A149), R =R^(A26), in L_(A150), R = R^(A27), in L_(A151), R = R^(A28), inL_(A152), R = R^(A29), in L_(A153), R = R^(A30), in L_(A154), R =R^(A31), in L_(A155), R = R^(A32), in L_(A156), R = R^(A33), inL_(A157), R = R^(A34), in L_(A158), R = R^(A35), in L_(A159), R =R^(A36), in L_(A160), R = R^(A37), in L_(A161), R = R^(A38), inL_(A162), R = R^(A39), in L_(A163), R = R^(A40), and in L_(A164), R =R^(A41),

wherein in L_(A165), R = R^(A1), in L_(A166), R = R^(A2), in L_(A167), R= R^(A3), in L_(A168), R = R^(A4), in L_(A169), R = R^(A5), in L_(A170),R = R^(A6), in L_(A171), R = R^(A7), in L_(A172), R = R^(A8), inL_(A173), R = R^(A9), in L_(A174), R = R^(A10), in L_(A175), R =R^(A11), in L_(A176), R = R^(A12), in L_(A177), R = R^(A13), inL_(A178), R = R^(A14), in L_(A179), R = R^(A15), in L_(A180), R =R^(A16), in L_(A181), R = R^(A17), in L_(A182), R = R^(A18), inL_(A183), R = R^(A19), in L_(A184), R = R^(A20), in L_(A185), R =R^(A21), in L_(A186), R = R^(A22), in L_(A187), R = R^(A23), inL_(A188), R = R^(A24), in L_(A189), R = R^(A25), in L_(A190), R =R^(A26), in L_(A191), R = R^(A27), in L_(A192), R = R^(A28), inL_(A193), R = R^(A29), in L_(A194), R = R^(A30), in L_(A195), R =R^(A31), in L_(A196), R = R^(A32), in L_(A197), R = R^(A33), inL_(A198), R = R^(A34), in L_(A199), R = R^(A35), in L_(A200), R =R^(A36), in L_(A201), R = R^(A37), in L_(A202), R = R^(A38), inL_(A203), R = R^(A39), in L_(A204), R = R^(A40), and in L_(A205), R =R^(A41);

wherein in L_(A206), R = R^(A1), in L_(A207), R = R^(A2), in L_(A208), R= R^(A3), in L_(A209), R = R^(A4), in L_(A210), R = R^(A5), in L_(A211),R = R^(A6), in L_(A212), R = R^(A7), in L_(A213), R = R^(A8), inL_(A214), R = R^(A9), in L_(A215), R = R^(A10), in L_(A216), R =R^(A11), in L_(A217), R = R^(A12), in L_(A218), R = R^(A13), inL_(A219), R = R^(A14), in L_(A220), R = R^(A15), in L_(A221), R =R^(A16), in L_(A222), R = R^(A17), in L_(A223), R = R^(A18), inL_(A224), R = R^(A19), in L_(A225), R = R^(A20), in L_(A226), R =R^(A21), in L_(A227), R = R^(A22), in L_(A228), R = R^(A23), inL_(A229), R = R^(A24), in L_(A230), R = R^(A25), in L_(A231), R =R^(A26), in L_(A232), R = R^(A27), in L_(A233), R = R^(A28), inL_(A234), R = R^(A29), in L_(A235), R = R^(A30), in L_(A236), R =R^(A31), in L_(A237), R = R^(A32), in L_(A238), R = R^(A33), inL_(A239), R = R^(A34), in L_(A240), R = R^(A35), in L_(A241), R =R^(A36), in L_(A242), R = R^(A37), in L_(A243), R = R^(A38), inL_(A244), R = R^(A39), in L_(A245), R = R^(A40), and in L_(A246), R =R^(A41);

wherein in L_(A247), R = R^(A1), in L_(A248), R = R^(A2), in L_(A249), R= R^(A3), in L_(A250), R = R^(A4), in L_(A251), R = R^(A5), in L_(A252),R = R^(A6), in L_(A253), R = R^(A7), in L_(A254), R = R^(A8), inL_(A255), R = R^(A9), in L_(A256), R = R^(A10), in L_(A257), R =R^(A11), in L_(A258), R = R^(A12), in L_(A259), R = R^(A13), inL_(A260), R = R^(A14), in L_(A261), R = R^(A15), in L_(A262), R =R^(A16), in L_(A263), R = R^(A17), in L_(A264), R = R^(A18), inL_(A265), R = R^(A19), in L_(A266), R = R^(A20), in L_(A267), R =R^(A21), in L_(A268), R = R^(A22), in L_(A269), R = R^(A23), inL_(A270), R = R^(A24), in L_(A271), R = R^(A25), in L_(A272), R =R^(A26), in L_(A273), R = R^(A27), in L_(A274), R = R^(A28), inL_(A275), R = R^(A29), in L_(A276), R = R^(A30), in L_(A277), R =R^(A31), in L_(A278), R = R^(A32), in L_(A279), R = R^(A33), inL_(A280), R = R^(A34), in L_(A281), R = R^(A35), in L_(A282), R =R^(A36), in L_(A283), R = R^(A37), in L_(A284), R = R^(A38), inL_(A285), R = R^(A39), in L_(A286), R = R^(A40), and in L_(A287), R =R^(A41);

wherein in L_(A288), R = R^(A1), in L_(A289), R = R^(A2), in L_(A290), R= R^(A3), in L_(A291), R = R^(A4), in L_(A292), R = R^(A5), in L_(A293),R = R^(A6), in L_(A294), R = R^(A7), in L_(A295), R = R^(A8), inL_(A296), R = R^(A9), in L_(A297), R = R^(A10), in L_(A298), R =R^(A11), in L_(A299), R = R^(A12), in L_(A300), R = R^(A13), inL_(A301), R = R^(A14), in L_(A302), R = R^(A15), in L_(A303), R =R^(A16), in L_(A304), R = R^(A17), in L_(A305), R = R^(A18), inL_(A306), R = R^(A19), in L_(A307), R = R^(A20), in L_(A308), R =R^(A21), in L_(A309), R = R^(A22), in L_(A310), R = R^(A23), inL_(A311), R = R^(A24), in L_(A312), R = R^(A25), in L_(A313), R =R^(A26), in L_(A314), R = R^(A27), in L_(A315), R = R^(A28), inL_(A316), R = R^(A29), in L_(A317), R = R^(A30), in L_(A318), R =R^(A31), in L_(A319), R = R^(A32), in L_(A320), R = R^(A33), inL_(A321), R = R^(A34), in L_(A322), R = R^(A35), in L_(A323), R =R^(A36), in L_(A324), R = R^(A37), in L_(A325), R = R^(A38), inL_(A326), R = R^(A39), in L_(A327), R = R^(A40), and in L_(A328), R =R^(A41);

wherein in L_(A329), R = R^(A1), in L_(A330), R = R^(A2), in L_(A331), R= R^(A3), in L_(A332), R = R^(A4), in L_(A333), R = R^(A5), in L_(A334),R = R^(A6), in L_(A335), R = R^(A7), in L_(A336), R = R^(A8), inL_(A337), R = R^(A9), in L_(A338), R = R^(A10), in L_(A339), R =R^(A11), in L_(A340), R = R^(A12), in L_(A341), R = R^(A13), inL_(A342), R = R^(A14), in L_(A343), R = R^(A15), in L_(A344), R =R^(A16), in L_(A345), R = R^(A17), in L_(A346), R = R^(A18), inL_(A347), R = R^(A19), in L_(A348), R = R^(A20), in L_(A349), R =R^(A21), in L_(A350), R = R^(A22), in L_(A351), R = R^(A23), inL_(A352), R = R^(A24), in L_(A353), R = R^(A25), in L_(A354), R =R^(A26), in L_(A355), R = R^(A27), in L_(A356), R = R^(A28), inL_(A357), R = R^(A29), in L_(A358), R = R^(A30), in L_(A359), R =R^(A31), in L_(A360), R = R^(A32), in L_(A361), R = R^(A33), inL_(A362), R = R^(A34), in L_(A363), R = R^(A35), in L_(A364), R =R^(A36), in L_(A365), R = R^(A37), in L_(A366), R = R^(A38), inL_(A367), R = R^(A39), in L_(A368), R = R^(A40), and in L_(A369), R =R^(A41);

wherein in L_(A370), R = R^(A1), in L_(A371), R = R^(A2), in L_(A372), R= R^(A3), in L_(A373), R = R^(A4), in L_(A374), R = R^(A5), in L_(A375),R = R^(A6), in L_(A376), R = R^(A7), in L_(A377), R = R^(A8), inL_(A378), R = R^(A9), in L_(A379), R = R^(A10), in L_(A380), R =R^(A11), in L_(A381), R = R^(A12), in L_(A382), R = R^(A13), inL_(A383), R = R^(A14), in L_(A384), R = R^(A15), in L_(A385), R =R^(A16), in L_(A386), R = R^(A17), in L_(A387), R = R^(A18), inL_(A388), R = R^(A19), in L_(A389), R = R^(A20), in L_(A390), R =R^(A21), in L_(A391), R = R^(A22), in L_(A392), R = R^(A23), inL_(A393), R = R^(A24), in L_(A394), R = R^(A25), in L_(A395), R =R^(A26), in L_(A396), R = R^(A27), in L_(A397), R = R^(A28), inL_(A398), R = R^(A29), in L_(A399), R = R^(A30), in L_(A400), R =R^(A31), in L_(A401), R = R^(A32), in L_(A402), R = R^(A33), inL_(A403), R = R^(A34), in L_(A404), R = R^(A35), in L_(A405), R =R^(A36), in L_(A406), R = R^(A37), in L_(A407), R = R^(A38), inL_(A408), R = R^(A39), in L_(A409), R = R^(A40), and in L_(A410), R =R^(A41);

wherein in L_(A411), R = R^(A1), in L_(A412), R = R^(A2), in L_(A413), R= R^(A3), in L_(A414), R = R^(A4), in L_(A415), R = R^(A5), in L_(A416),R = R^(A6), in L_(A417), R = R^(A7), in L_(A418), R = R^(A8), inL_(A419), R = R^(A9), in L_(A420), R = R^(A10), in L_(A421), R =R^(A11), in L_(A422), R = R^(A12), in L_(A423), R = R^(A13), inL_(A424), R = R^(A14), in L_(A425), R = R^(A15), in L_(A426), R =R^(A16), in L_(A427), R = R^(A17), in L_(A428), R = R^(A18), inL_(A429), R = R^(A19), in L_(A430), R = R^(A20), in L_(A431), R =R^(A21), in L_(A432), R = R^(A22), in L_(A433), R = R^(A23), inL_(A434), R = R^(A24), in L_(A435), R = R^(A25), in L_(A436), R =R^(A26), in L_(A437), R = R^(A27), in L_(A438), R = R^(A28), inL_(A439), R = R^(A29), in L_(A440), R = R^(A30), in L_(A441), R =R^(A31), in L_(A442), R = R^(A32), in L_(A443), R = R^(A33), inL_(A444), R = R^(A34), in L_(A445), R = R^(A35), in L_(A446), R =R^(A36), in L_(A447), R = R^(A37), in L_(A448), R = R^(A38), inL_(A449), R = R^(A39), in L_(A450), R = R^(A40), and in L_(A451), R =R^(A41);

-   -   wherein, R^(A1) through R^(A41) have the formulas:

In one embodiment, where the first compound has a structure according tothe formula of Ir(L¹)₂(L²), L¹ is selected from the group consisting ofL_(A1) through L_(A450), and L_(A451), and L² is selected from the groupconsisting of

In the above structures, the dash line represents the bond between thecurrent group and the next group to which it attaches. For example, inL_(A1), dash lines represent the bonds between the M and the ligand; inR^(A1), dash line represents the bond between R and the aromatic ring.

In another embodiment, the first compound is selected from the groupconsisting of Compound 1 through Compound 5,863, wherein each ofCompound x, where x=451j+k−451, k is an integer from 1 to 451, and j isan integer from 1 to 13, has the formula Ir(L_(Ak))₂(L_(Bj)). L_(A1)through L_(A451) and L_(B1) through L_(B13) are as defined above.

The examples of the first compound disclosed herein are metal complexesbased on ligands containing 1-phenylisoquinoline, 2-phenylquinoline,8-(quinolin-2-yl)benzofuro[2,3-b]pyridine,8-(isoquinolin-1-yl)benzofuro[2,3-b]pyridine,4-(4-fluorophenyl)quinazoline, or 2-phenylpyridine, etc. Each of theligands contain at least one alkylated side chain which contains atleast one fluorine atom that is not benzylic. The presence of these sidechains provide a fine tuning of the color of the metal complex mostly asa slight red shift. The shorter the spacer in between the aromatic unitand the fluorine atom, the greater the red shift in the final complexwill be. Good efficiencies were observed from these compounds. Moreimportantly, it was unexpectedly discovered that the inventive compoundsshowed much better lifetime than compounds with fluorine at the benzylicposition. Previous compounds with trifluoromethyl substitution andperfluoro alkyl substitution have shown very poor device stability.

According to another aspect, a first device comprising a first organiclight emitting device is disclosed. The first organic light emittingdevice comprises: an anode; a cathode; and an organic layer, disposedbetween the anode and the cathode. The organic layer comprises the firstcompound as disclosed herein. The first compound incorporated into thefirst device can be any one or more of the embodiments and variations ofthe first compound disclosed herein. For example, the first compound iscapable of functioning as a phosphorescent emitter at room temperatureand wherein the first compound has at least one aromatic ring and atleast one substituent R, wherein each of the at least one substituent Ris independently selected from the group consisting of partiallyfluorinated alkyl, partially fluorinated cycloalkyl, and combinationsthereof; wherein each of the at least one substituent R is directlybonded to one of the aromatic rings; and wherein in each of the at leastone substituent R, C having an F attached thereto is separated by atleast one carbon atom from the aromatic ring.

According to an embodiment, the first device is selected from the groupconsisting of a consumer product, an electronic component module, anorganic light emitting device, and a lighting panel.

In the first device, the organic layer is an emissive layer and thecompound is an emissive dopant.

In one embodiment of the first device, the organic layer furthercomprises a host; wherein the host comprises a triphenylene containingbenzo-fused thiophene or benzo-fused furan; wherein any substituent inthe host material is an unfused substituent independently selected fromthe group consisting of C_(n)H_(2n+1), OC_(n)H_(2n+1), OAr₁,N(C_(n)H_(2n+1))₂, N(Ar₁)(Ar₂), CH═CH—C_(n)H_(2n+1), C≡C—C_(n)H_(2n+1),Ar₁, Ar₁-Ar₂, C_(n)H_(2n)—Ar₁, or no substitution; wherein n is from 1to 10; and wherein Ar₁ and Ar₂ are independently selected from the groupconsisting of benzene, biphenyl, naphthalene, triphenylene, carbazole,and heteroaromatic analogs thereof.

The host in the first device can comprise at least one chemical groupselected from the group consisting of triphenylene, carbazole,dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene,azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, andaza-dibenzoselenophene.

The host can be selected from the group consisting of:

and combinations thereof.

In the first device, the host material comprises a metal complex.

In yet another aspect of the present disclosure, a formulation thatcomprises the compound having at least one non-conjugated substituent Rselected from the group consisting of C_(n)H_(2n+1−m)F_(m) andC_(q)H_(2q−1−m)F_(m), wherein R is directly bonded to an aromatic ring.n is an integer greater than 1, q is an integer greater than 2, and m isan integer greater than 0, wherein C having F attaching to is separatedby at least one carbon atom from the aromatic ring is disclosed. Theformulation can also include one or more components selected from thegroup consisting of a solvent, a host, a hole injection material, holetransport material, and an electron transport layer material, disclosedherein.

Materials Synthesis

All reactions were carried out under nitrogen protections unlessspecified otherwise. All solvents for reactions are anhydrous and usedas received from commercial sources.

Synthesis of Comparative Compound 1 Synthesis of(2-amino-6-(trifluoromethyl)phenyl)methanol

2-amino-6-(trifluoromethyl)benzoic acid (20 g, 97 mmol) was dissolved intetrahydrofuran (120 mL) in a 3-neck RB flask equipped with an additionfunnel and a condenser. The solution was cooled in an ice-water bath.LiAlH₄ (83 mL, 166 mmol) (2M solution in THF) was then added dropwise.After all of the LiAlH₄ solution was added, the reaction mixture wasallowed to warm to room temperature and stirred at room temperatureovernight. The reaction was then quenched by adding 10 mL of Water, then10 mL of 15% NaOH and then 25 mL of Water. The salts were filtered offand the solvents were evaporated under vacuum. The product was used asis (18 g, 97% yield).

Synthesis of 2-(3,5-dimethylphenyl)-5-(trifluoromethyl)quinoline

A mixture of (2-amino-6-(trifluoromethyl)phenyl)methanol (18 g, 94mmol), 1-(3,5-dimethylphenyl)ethanone (19.5 ml, 130 mmol), powderedpotassium hydroxide (0.90 g, 16.0 mmol), and RuCl₂(PPh₃)₃ (0.45 g, 0.47mmol) in toluene (310 ml) was refluxed overnight. Upon cooling to roomtemperature, the mixture was washed with water and extracted with ethylacetate (3 times). The crude material was coated on celite and purifiedby CC starting with 5% EA in Heptanes. The product obtained wasrecrystallized from methanol to afford2-(3,5-dimethylphenyl)-5-(trifluoromethyl)quinoline (10 g, 35% yield) asyellow crystals.

Synthesis of Ir(III) Dimer

2-(3,5-dimethylphenyl)-5-(trifluoromethyl)quinoline (3.00 g, 9.96 mmol)was solubilized in ethoxyethanol (30 mL) and water (10 mL) and degassedwith nitrogen for 30 minutes. Iridium chloride (0.92 g, 2.49 mmol) wasthen added to the solution and the reaction was refluxed under nitrogenfor 24 hours. After cooling down to room temperature, the solid wasfiltered, washed with methanol and dried to give Ir(III) Dimer (1.0 g,49% yield) as a brown powder.

Synthesis of Comparative Compound 1

The Ir(III) Dimer (1.08 g, 0.65 mmol) and 3,7-diethylnonane-4,6-dione(1.38 g, 6.52 mmol) were diluted in ethoxyethanol (22 mL) and themixture was degassed by bubbling nitrogen gas for 15 minutes. K₂CO₃(0.90 g, 6.52 mmol) was then added and the reaction was stirred at roomtemperature overnight. The mixture was diluted with dichloromethane(“DCM”), filtered through a pad of Celite, and washed with DCM. Thecrude material was purified by column chromatography (silica pre-treatedwith triethylamine (TEA)) using Heptanes/DCM 80/20 solvent system. Thecollected pure fractions were triturated from methanol and the solidswere recrystallized from dichloromethane/methanol to afford theComparative Compound 1 (0.85 g, 65% yield) as a dark red powder.

Synthesis of Compound 453 Synthesis of2-(3,5-dimethylphenyl)-5-(3,3,3-trifluoropropyl)quinoline

5-bromo-2-(3,5-dimethylphenyl)quinoline (1.15 g, 3.68 mmol),Palladium(II) acetate (0.017 g, 0.074 mmol), and CPhos (0.064 g, 0.147mmol) were charged into a flask and diluted with 100 mL oftetrahydrofuran. This mixture was degassed with nitrogen followed by theaddition of (3,3,3-trifluoropropyl)zinc(II) iodide (1.07 g, 3.68 mmol)via syringe. The reaction mixture was stirred at room temperatureovernight. The reaction mixture was quenched with aqueous ammoniumchloride then was extracted 2×200 mL of ethyl acetate, and dried oversodium sulfate. The crude material was coated on Celite and purified bycolumn chromatography using a 20% DCM in Heptanes solvent system. Theproduct was recrystallized in heptanes to afford 0.90 g of the targetcompound (81% yield).

Synthesis of Ir(III) Dimer

2-(3,5-dimethylphenyl)-5-(3,3,3-trifluoropropyl)quinoline (1.80 g, 5.47mmol) was solubilized in ethoxyethanol (15 mL) and Water (5 mL) anddegassed with nitrogen for 30 minutes. Iridium Chloride (0.54 g, 1.46mmol) was then added to the solution and the reaction was refluxed undernitrogen for 24 hours. After cooling down to room temperature, the solidwas filtered, washed with methanol and dried to give Ir(III) Dimer (0.95g, 74% yield) as a brown powder.

Synthesis of Compound 453

The Ir(III) Dimer (0.95 g, 0.537 mmol) and 3,7-diethylnonane-4,6-dione(1.14 g, 5.37 mmol) were diluted in ethoxyethanol (15 mL) and themixture was degassed by bubbling nitrogen gas for 15 minutes. K₂CO₃(0.74 g, 5.37 mmol) was then added and the reaction was stirred at roomtemperature overnight. The mixture was diluted with DCM, filteredthrough a pad of Celite, and washed with DCM. The crude material waspurified by column chromatography (silica pre-treated with TEA) usingHeptanes/DCM (100/0 to 97/3) solvent system. The collected purefractions were triturated from methanol and the solids wererecrystallized from dichloromethane/methanol to afford Compound 453(0.83 g, 73% yield) as a dark red powder.

Synthesis of Compound 781 Synthesis of2,6-dimethyl-8-(5-(3,3,3-trifluoropropyl)quinolin-2-yl)benzofuro[2,3-b]pyridine

8-(5-chloroquinolin-2-yl)-2,6-dimethylbenzofuro[2,3-b]pyridine (3.40 g,9.48 mmol),2′-(dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine(0.33 g, 0.76 mmol) and diacetoxypalladium (0.09 g, 0.38 mmol) werecharged into a flask and diluted with THF (150 mL). This mixture wasdegassed by bubbling nitrogen followed by the addition of(3,3,3-trifluoropropyl)zinc(II) iodide (40 mL, 11.8 mmol) via syringe.This mixture was stirred at room temperature overnight. Upon completionof the reaction, it was quenched with aqueous ammonium chloride then wasextracted two times with 200 mL ethyl acetate. These extracts were driedover magnesium sulfate then were filtered and concentrated under vacuum.The crude residue was purified by column chromatography using 20/80Ethyl Acetate/Heptanes. The combined fractions were triturated inHeptanes to afford2,6-dimethyl-8-(5-(3,3,3-trifluoropropyl)quinolin-2-yl)benzofuro[2,3-b]pyridine(2.55 g, 64% yield) as an off-white powder.

Synthesis of Ir(III) Dimer

2,6-dimethyl-8-(5-(3,3,3-trifluoropropyl)quinolin-2-yl)benzofuro[2,3-b]pyridine(2.55 g, 6.07 mmol) was solubilized in 2-ethoxyethanol (19 mL) and water(6 mL) and degassed by bubbling nitrogen for 30 minutes. IridiumChloride (0.56 g, 1.52 mmol) was then added to the solution (some ligandhad precipitated) and the reaction was refluxed under nitrogen for 24hours. After cooling down to room temperature, the solid was filtered,washed with methanol and dried to give Ir(III) Dimer (1.10 g, 68% yield)as a red powder.

Synthesis of Compound 781

The Ir(III) Dimer (1.00 g, 0.47 mmol) and 3,7-diethylnonane-4,6-dione(0.91 g, 4.26 mmol) were diluted in 2-Ethoxyethanol (14 mL) and themixture was degassed by bubbling nitrogen gas for 15 minutes. K₂CO₃(0.59 g, 4.26 mmol) was then added and the reaction was stirred at roomtemperature overnight. The mixture was diluted with dichloromethane,filtered through a pad of Celite, and washed with DCM. The crudematerial was purified by column chromatography (silica pre-treated withTEA) using Heptanes/dichloromethane 80/20 solvent system. The combinedfractions were triturated from methanol and the solids wererecrystallized from dichloromethane/methanol once. The title product wasobtained as a red powder (0.8 g, 76% yield).

Synthesis of Compound 699 Synthesis of2-(4-fluoro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

5-bromo-2-fluoro-1,3-dimethylbenzene (20 g, 100 mmol),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (51 g, 200mmol), Pd₂(dba)₃ (1.83 g, 2.00 mmol),dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SPhos)(3.28 g, 8.00 mmol), potassium acetate (24.5 g, 250 mmol) and dioxane(600 mL) were combined in a three neck round bottom flask. A condenserwas attached then the system was evacuated and purged with nitrogenthree times. The reaction was heated to reflux overnight. Uponcompletion, the reaction was filtered through celite and washed withethyl acetate. The filtrate was concentrated down to a dark red oilwhich was dissolved in 400 mL heptane and loaded on to a silica gel plugin a sintered filter funnel. The silica gel was washed with 2 L heptaneportion then one 1 L of 98/2 heptane/ethyl acetate to recover most ofthe product and remove the bispinocolate. These portions were combinedand concentrated down to 30 g of yellow oil which was purified withsilica gel using heptane to 95/5 heptane/ethyl acetate solvent system.Fractions containing the desired product were combined and concentrateddown to 17.5 g of a light yellow solid for a 70% yield.

Synthesis of 7-chloro-4-(4-fluoro-3,5-dimethylphenyl)quinazoline

4,7-dichloroquinazoline (4.0 g, 20.1 mmol),2-(4-fluoro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(5.53 g, 22.1 mmol), sodium carbonate (5.33 g, 50.2 mmol), palladiumtetrakis (0.70 g, 0.60 mmol), dimethoxyethane (“DME”) (160 mL), andwater (40 mL) were combined in a three neck round bottom flask. Acondenser was attached then the system was evacuated and purged withnitrogen three times. The reaction was heated to a vigorous refluxovernight. The reaction was diluted with ethyl acetate, water and brine.The aqueous was partitioned off and the organic was washed once withbrine, dried with sodium sulfate, filtered then concentrated down to ayellow solid. The yellow solid was purified with silica gel using DCM to85/15 DCM/ethyl acetate solvent system to get 4.1 g of light yellowsolid for a 71% yield.

Synthesis of 4-(4-fluoro-3,5-dimethylphenyl)-7-(3,3,3-trifluoropropyl)quinazoline

7-chloro-4-(4-fluoro-3,5-dimethylphenyl)quinazoline (2.75 g, 9.59 mmol),2′-(dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine(CPhos) (0.34 g, 0.77 mmol), and diacetoxypalladium (0.090 g, 0.38 mmol)and 100 mL anhydrous THF were placed in an oven dried three neck roundbottom flask. The system was evacuated and purged with nitrogen threetimes. (3,3,3-trifluoropropyl)zinc(II) iodide (86 ml, 19.2 mmol) wasadded via syringe. Upon completion of the reaction, it was quenched withammonium chloride solution then transferred to a separatory funnel withethyl acetate. The aqueous was partitioned off, then the organics werewashed once with brine, dried with sodium sulfate, filtered andconcentrated down. The crude solid was purified with silica gel usingDCM to 90/10 DCM/ethyl acetate solvent system to get 3.3 g of abrownish-red solid. The 3.3 g solid was purified using C18 cartridgesusing 80/20 to 85/15 acetonitrile/water solvent system. The combinedfractions were concentrated down then dried in the vacuum oven overnightto get 2.36 g of a white solid for a 71% yield.

Synthesis of Ir(III) Dimer

4-(4-fluoro-3,5-dimethylphenyl)-7-(3,3,3-trifluoropropyl)quinazoline(2.56 g, 7.34 mmol) was inserted in a RBF and was solubilized inethoxythanol (23 mL) and water (8 mL). The mixture was degassed bybubbling nitrogen gas for 15 minutes and then iridium chloride (0.68 g,1.84 mmol) was inserted and the reaction was heated at 105° C. for 24hours. The reaction was cooled down to room temperature, diluted with 10mL of MeOH, filtered and washed with MeOH. The Ir(III) Dimer (1.50 g,89% yield) was afforded as an orange powder.

Synthesis of Compound 681

The dimer (1.50 g, 0.81 mmol), 3,7-diethylnonane-4,6-dione (1.73 g, 8.13mmol), and 2-ethoxyethanol (50 ml) were combined round bottom flask.Nitrogen was bubbled directly into the suspension for 15 min. Potassiumcarbonate (1.12 g, 8.13 mmol) was added and the reaction was run at roomtemperature overnight. Upon completion, the reaction was filteredthrough celite using DCM until the red color came off. The solution wasconcentrated down to a dark red oily solid, taken up in DCM and adsorbedon to celite. The sample was purified with silica gel to give 0.24 g ofdark red solid for a 13% yield.

Synthesis of Compound 22 Synthesis of(4,4,4-trifluoro-3-(trifluoromethyl)butyl)zinc(II) iodide

Lithium chloride (1.87 g, 44.1 mmol) was charged into a reaction flask.The flask was evacuated and heated using a heat gun for 10 minutes. Theflask was cooled to room temperature and zinc (2.88 g, 44.1 mmol) wasadded to the flask. The flask was again evacuated and heated using aheat gun for 10 minutes. The flask was cooled to room temperature andTHF (80 mL) was syringed into the reaction followed by 1,2-dibromoethane(0.42 mL, 4.90 mmol). This mixture was stirred for 30 minutes in an oilbath set at 60° C. The mixture was cooled to room temperature followedby the addition of chlorotrimethylsilane (0.12 ml, 0.98 mmol) anddiiodine (0.25 g, 0.98 mmol) dissolved in 4 mL of THF. The mixture wasagain stirred for 30 minutes in an oil bath set at 60° C. The mixturewas again cooled to room temperature.1,1,1-trifluoro-4-iodo-2-(trifluoromethyl)butane (7.50 g, 24.5 mmol) wasthen injected into the reaction mixture via syringe. The heterogeneousreaction mixture was stirred and heated in an oil bath set at 50° C.overnight. The reaction mixture was cooled to room temperature andstirring was stopped. The product was used as is.

Synthesis of2-(3,5-dimethylphenyl)-5-(4,4,4-trifluoro-3-(trifluoromethyl)butyl)quinoline

8-(5-chloroquinolin-2-yl)-2,6-dimethylbenzofuro[2,3-b]pyridine (3.40 g,9.48 mmol),2′-(dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine(CPhos) (0.33 g, 0.76 mmol) and diacetoxypalladium (0.09 g, 0.38 mmol)were diluted with THF (190 mL). This mixture was degassed by bubblingnitrogen gas for 15 minutes followed by the addition of(3,3,3-trifluoropropyl)zinc(II) iodide (35 mL, 10.4 mmol) via syringe.This mixture was stirred at room temperature overnight. Upon completionof the reaction, the mixture was quenched with aqueous ammonium chloridethen was extracted with 2×200 mL ethyl acetate. These extracts weredried over magnesium sulfate then were filtered and concentrated undervacuum. The crude material was purified via column chromatography usingHeptanes/EA (95/5 to 90/10) solvent system. The product was trituratedwith methanol and then recrystallized from Heptanes to afford2-(3,5-dimethylphenyl)-5-(4,4,4-trifluoro-3-(trifluoromethyl)butyl)quinoline(2.5 g, 51% yield) as a white solid.

Synthesis of Ir(III) Dimer

2-(3,5-dimethylphenyl)-5-(4,4,4-trifluoro-3-(trifluoromethyl)butyl)quinoline(2.48 g, 6.02 mmol) was inserted in a round-bottom flask and wassolubilized in Ethoxythanol (24 mL) and Water (8 mL). The mixture wasdegassed by bubbling nitrogen gas for 15 minutes and then IridiumChloride (0.72 g, 1.94 mmol) was inserted and the reaction was heated at105° C. for 24 hours. The reaction was cooled down to room temperature,diluted with 10 mL of MeOH, filtered and washed with MeOH to afford theIr(III) Dimer (1.2 g, 59% yield)

Synthesis of Compound 22

The Ir(III) Dimer (0.50 g, 0.24 mmol) was solubilized in Ethoxyethanol(8 mL) and pentane-2,4-dione (0.25 mL, 2.39 mmol) was added. The mixturewas degassed by bubbling nitrogen gas for 15 minutes and K₂CO₃ (0.33 g,2.39 mmol) was then added and the reaction was stirred at roomtemperature overnight. Upon completion of the reaction, the mixture wasdiluted with DCM, filtered through celite and washed with DCM. The crudeproduct was coated on Celite and purified via column chromatography (TEApretreated) using Heptanes/DCM (95/5) solvent system. The product wasrecrystallized several times (5 times) from MeOH/DCM, EtOH/DCM, andTHF/i-PrOH to afford 0.18 g (34% yield) of the target compound.

Synthesis of Compound 473

The Ir(III) Dimer (0.70 g, 0.33 mmol) was solubilized in Ethoxyethanol(15 mL) and 3,7-diethylnonane-4,6-dione (0.71 g, 3.34 mmol) was added.The mixture was degassed by bubbling nitrogen gas for 15 minutes andK₂CO₃ (0.46 g, 3.34 mmol) was then added and the reaction was stirred atroom temperature overnight. Upon completion of the reaction, the mixturewas diluted with DCM, filtered through celite and washed with DCM. Thecrude product was coated on Celite and purified via columnchromatography (TEA pretreated) using Heptanes/DCM (95/5 to 90/10)solvent system. The product was triturated from methanol to afford 0.21g (26% yield) of the dopant.

Combination with Other Materials

The materials described herein as useful for a particular layer in anorganic light emitting device may be used in combination with a widevariety of other materials present in the device. For example, emissivedopants disclosed herein may be used in conjunction with a wide varietyof hosts, transport layers, blocking layers, injection layers,electrodes and other layers that may be present. The materials describedor referred to below are non-limiting examples of materials that may beuseful in combination with the compounds disclosed herein, and one ofskill in the art can readily consult the literature to identify othermaterials that may be useful in combination.

HIL/HTL:

A hole injecting/transporting material to be used in the presentinvention is not particularly limited, and any compound may be used aslong as the compound is typically used as a hole injecting/transportingmaterial. Examples of the material include, but not limit to: aphthalocyanine or porphyrin derivative; an aromatic amine derivative; anindolocarbazole derivative; a polymer containing fluorohydrocarbon; apolymer with conductivity dopants; a conducting polymer, such asPEDOT/PSS; a self-assembly monomer derived from compounds such asphosphonic acid and silane derivatives; a metal oxide derivative, suchas MoO_(x); a p-type semiconducting organic compound, such as1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and across-linkable compounds.

Examples of aromatic amine derivatives used in HIL or HTL include, butnot limit to the following general structures:

Each of Ar¹ to Ar⁹ is selected from the group consisting of aromatichydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl,triphenylene, naphthalene, anthracene, phenalene, phenanthrene,fluorene, pyrene, chrysene, perylene, and azulene; the group consistingof aromatic heterocyclic compounds such as dibenzothiophene,dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran,benzothiophene, benzoselenophene, carbazole, indolocarbazole,pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole,oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole,pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine,oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine,benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline,cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine,pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine,benzofuropyridine, furodipyridine, benzothienopyridine,thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine;and the group consisting of 2 to 10 cyclic structural units which aregroups of the same type or different types selected from the aromatichydrocarbon cyclic group and the aromatic heterocyclic group and arebonded to each other directly or via at least one of oxygen atom,nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom,chain structural unit and the aliphatic cyclic group. Wherein each Ar isfurther substituted by a substituent selected from the group consistingof hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl,arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl,heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylicacids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl,phosphino, and combinations thereof.

In one aspect, Ar¹ to Ar⁹ is independently selected from the groupconsisting of:

wherein k is an integer from 1 to 20; X¹⁰¹ to X¹⁰⁸ is C (including CH)or N; Z¹⁰¹ is NAr¹, O, or S; Ar¹ has the same group defined above.

Examples of metal complexes used in HIL or HTL include, but not limit tothe following general formula:

wherein Met is a metal, which can have an atomic weight greater than 40;(Y¹⁰¹-Y¹⁰²) is a bidentate ligand, Y¹⁰¹ and Y¹⁰² are independentlyselected from C, N, O, P, and S; L¹⁰¹ is an ancillary ligand; k′ is aninteger value from 1 to the maximum number of ligands that may beattached to the metal; and k′+k″ is the maximum number of ligands thatmay be attached to the metal.

In one aspect, (Y¹⁰¹-Y¹⁰²) is a 2-phenylpyridine derivative. In anotheraspect, (Y¹⁰¹-Y¹⁰²) is a carbene ligand. In another aspect, Met isselected from Ir, Pt, Os, and Zn. In a further aspect, the metal complexhas a smallest oxidation potential in solution vs. Fc⁺/Fc couple lessthan about 0.6 V.

Host:

The light emitting layer of the organic EL device of the presentinvention preferably contains at least a metal complex as light emittingmaterial, and may contain a host material using the metal complex as adopant material. Examples of the host material are not particularlylimited, and any metal complexes or organic compounds may be used aslong as the triplet energy of the host is larger than that of thedopant. While the Table below categorizes host materials as preferredfor devices that emit various colors, any host material may be used withany dopant so long as the triplet criteria is satisfied.

Examples of metal complexes used as host are preferred to have thefollowing general formula:

wherein Met is a metal; (Y¹⁰³-Y¹⁰⁴) is a bidentate ligand, Y¹⁰³ and Y¹⁰⁴are independently selected from C, N, O, P, and S; L¹⁰¹ is an anotherligand; k′ is an integer value from 1 to the maximum number of ligandsthat may be attached to the metal; and k′+k″ is the maximum number ofligands that may be attached to the metal.

In one aspect, the metal complexes are:

wherein (O—N) is a bidentate ligand, having metal coordinated to atoms Oand N.

In another aspect, Met is selected from Ir and Pt. In a further aspect,(Y¹⁰³-Y¹⁰⁴) is a carbene ligand.

Examples of organic compounds used as host are selected from the groupconsisting of aromatic hydrocarbon cyclic compounds such as benzene,biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene,phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; thegroup consisting of aromatic heterocyclic compounds such asdibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene,benzofuran, benzothiophene, benzoselenophene, carbazole,indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole,triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole,thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine,oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole,indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline,isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine,phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine,phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine,thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine;and the group consisting of 2 to 10 cyclic structural units which aregroups of the same type or different types selected from the aromatichydrocarbon cyclic group and the aromatic heterocyclic group and arebonded to each other directly or via at least one of oxygen atom,nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom,chain structural unit and the aliphatic cyclic group. Wherein each groupis further substituted by a substituent selected from the groupconsisting of hydrogen, deuterium, halide, alkyl, cycloalkyl,heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl,cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl,carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl,sulfonyl, phosphino, and combinations thereof.

In one aspect, the host compound contains at least one of the followinggroups in the molecule:

wherein R¹⁰¹ to R¹⁰⁷ is independently selected from the group consistingof hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl,arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl,heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylicacids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl,phosphino, and combinations thereof, when it is aryl or heteroaryl, ithas the similar definition as Ar's mentioned above. k is an integer from0 to 20 or 1 to 20; k′″ is an integer from 0 to 20. X¹⁰¹ to X¹⁰⁸ isselected from C (including CH) or N.Z¹⁰¹ and Z¹⁰² is selected from NR¹⁰¹, O, or S.

HBL:

A hole blocking layer (HBL) may be used to reduce the number of holesand/or excitons that leave the emissive layer. The presence of such ablocking layer in a device may result in substantially higherefficiencies as compared to a similar device lacking a blocking layer.Also, a blocking layer may be used to confine emission to a desiredregion of an OLED.

In one aspect, compound used in HBL contains the same molecule or thesame functional groups used as host described above.

In another aspect, compound used in HBL contains at least one of thefollowing groups in the molecule:

wherein k is an integer from 1 to 20; L¹⁰¹ is an another ligand, k′ isan integer from 1 to 3.

ETL:

Electron transport layer (ETL) may include a material capable oftransporting electrons. Electron transport layer may be intrinsic(undoped), or doped. Doping may be used to enhance conductivity.Examples of the ETL material are not particularly limited, and any metalcomplexes or organic compounds may be used as long as they are typicallyused to transport electrons.

In one aspect, compound used in ETL contains at least one of thefollowing groups in the molecule:

wherein R¹⁰¹ is selected from the group consisting of hydrogen,deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy,aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl,aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile,isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinationsthereof, when it is aryl or heteroaryl, it has the similar definition asAr's mentioned above. Ar¹ to Ar³ has the similar definition as Ar'smentioned above. k is an integer from 1 to 20. X¹⁰¹ to X¹⁰⁸ is selectedfrom C (including CH) or N.

In another aspect, the metal complexes used in ETL contains, but notlimit to the following general formula:

wherein (O—N) or (N—N) is a bidentate ligand, having metal coordinatedto atoms O, N or N, N; L¹⁰¹ is another ligand; k′ is an integer valuefrom 1 to the maximum number of ligands that may be attached to themetal.

In any above-mentioned compounds used in each layer of the OLED device,the hydrogen atoms can be partially or fully deuterated. Thus, anyspecifically listed substituent, such as, without limitation, methyl,phenyl, pyridyl, etc. encompasses undeuterated, partially deuterated,and fully deuterated versions thereof. Similarly, classes ofsubstituents such as, without limitation, alkyl, aryl, cycloalkyl,heteroaryl, etc. also encompass undeuterated, partially deuterated, andfully deuterated versions thereof.

In addition to and/or in combination with the materials disclosedherein, many hole injection materials, hole transporting materials, hostmaterials, dopant materials, exiton/hole blocking layer materials,electron transporting and electron injecting materials may be used in anOLED. Non-limiting examples of the materials that may be used in an OLEDin combination with materials disclosed herein are listed in Table Abelow. Table A lists non-limiting classes of materials, non-limitingexamples of compounds for each class, and references that disclose thematerials.

TABLE A MATERIAL EXAMPLES OF MATERIAL PUBLICATIONS Hole injectionmaterials Phthalocyanine and porphyrin compounds

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Appl. Phys. Lett. 78, 673 (2001) Conducting polymers (e.g., PEDOT:PSS,polyaniline, polythiophene

Synth. Met. 87, 171 (1997) WO2007002683 Phosphonic acid and silane SAMs

US20030162053 Triarylamine or polythiophene polymers with conductivitydopants

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Organic compounds with conductive inorganic compounds, such asmolybdenum and tungsten oxides

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US20020158242 Metal organometallic complexes

US20060240279 Cross-linkable compounds

US20080220265 Polythiophene based polymers and copolymers

WO 2011075644 EP2350216 Hole transporting materials Triarylamines (e.g.,TPD, α-NPD)

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Appl. Phys. Lett. 90, 183503 (2007)

Appl. Phys. Lett. 90, 183503 (2007) Triarylamine on spirofluorene core

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Adv. Mater. 6, 677 (1994), US20080124572 Triarylamine with (di)benzo-thiophene/(di) benzofuran

US20070278938, US20080106190 US20110163302 Indolocarbazoles

Synth. Met. 111, 421 (2000) Isoindole compounds

Chem. Mater. 15, 3148 (2003) Metal carbene complexes

US20080018221 Phosphorescent OLED host materials Red hostsArylcarbazoles

Appl. Phys. Lett. 78, 1622 (2001) Metal 8- hydroxyquinolates (e.g.,Alq₃, BAlq)

Nature 395, 151 (1998)

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WO2005014551

WO2006072002 Metal phenoxy- benzothiazole compounds

Appl. Phys. Lett. 90, 123509 (2007) Conjugated oligomers and polymers(e.g., polyfluorene)

Org. Electron. 1, 15 (2000) Aromatic fused rings

WO2009066779, WO2009066778, WO2009063833, US20090045731, US20090045730,WO2009008311, US20090008605, US20090009065 Zinc complexes

WO2010056066 Green hosts Chrysene based compounds

WO2011086863 Arylcarbazoles

Appl. Phys. Lett. 78, 1622 (2001)

US20030175553

WO2011039234 Aryltriphenylene compounds

US20060280965

US20060280965

WO2009021126 Poly-fused heteroaryl compounds

US20090309488 US20090302743 US20100012931 Donor acceptor type molecules

WO2008056746

WO2010107244 Aza-carbazole/ DBT/DBF

JP2008074939

US20100187984 Polymers (e.g., PVK)

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EXPERIMENTAL Device Examples

All example devices were fabricated by high vacuum (<10⁻⁷ Torr) thermalevaporation. The anode electrode was 1200 Å of indium tin oxide (ITO).The cathode consisted of 10 Å of LiF followed by 1,000 Å of Al. Alldevices were encapsulated with a glass lid sealed with an epoxy resin ina nitrogen glove box (<1 ppm of H₂O and O₂) immediately afterfabrication, and a moisture getter was incorporated inside the package.The organic stack of the device examples consisted of sequentially, fromthe ITO surface, 100 Å of LG101 (purchased from LG chem) as the holeinjection layer (HIL); 400 Å of4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD) as the holetransporting layer (HTL); 300 Å of an emissive layer (EML) containingCompound H as a host (79%), a stability dopant (SD) (18%), and Compound453, Compound 781, or Compound 699 as an emitter; 100 Å of Compound H asa blocking layer; and 450 Å of Alq₃ (tris-8-hydroxyquinoline aluminum)as the ETL. The emitter was selected to provide the desired color andthe stability dopant (SD) was mixed with the electron-transporting hostand the emitter to help transport positive charge in the emissive layer.The Comparative Example device was fabricated similarly to the deviceexamples except that Comparative Compound 1 was used as the emitter inthe EML. Table 1 shows the composition of the EML in the device, whilethe device results and data are summarized in Table 2. As used herein,NPD, compound H, SD, and AlQ₃ have the following structures:

Comparative Examples

Comparative Compound 1 used in the experiments has the followingstructure

Inventive Compounds:

Representative inventive compounds Compound 453, Compound 781, Compound699, Compound 22, and Compound 473 used in the experiments have thefollowing structures:

Table 1 below lists the compounds used as the emitter dopants in the EMLlayer of the experimental devices.

TABLE 1 Example Emitter Inventive Device Example 1 Compound 453Inventive Device Example 2 Compound 781 Inventive Device Example 3Compound 699 Inventive Device Example 4 Compound 22 Inventive DeviceExample 5 Compound 473 Comparative Device example 1 Comparative compound1

Table 2 below provides the device performance data for Inventive DeviceExamples 1, 2, 3, 4 and 5 and Comparative Device example 1.

TABLE 2 EQE at LT_(95%) at 1931 CIE λ max 1,000 nits 1,000 nits X y [nm][cd/A] [h] Inventive 0.65 0.35 620 1.74 8.55 Device Example 1 Inventive0.64 0.36 614 1.74 9.09 Device Example 2 Inventive 0.66 0.34 618 1.825.73 Device Example 3 Inventive 0.65 0.35 627 1.64 1.53 Device Example 4Inventive 0.65 0.35 624 1.80 1.54 Device Example 5 Comparative 0.66 0.34644 1.00 1.00 example 1

Table 2 summarizes the performance of the experimental devices. The 1931CIE values were measured at 10 mA/cm². The luminous efficiency wasmeasured at 1000 cd/m². The EQE, and LT_(95%) of comparative example 1were set at a value of 1.00. The values obtained from the inventiveexamples are relative to that of the comparative example. All of theInventive Device Examples exhibit higher external quantum efficiencies(EQE) than the Comparative example 1 (1.74, 1.74, 1.82, 1.64, 1.80 vs.1.00). The lifetime represented by LT_(95%) at 1,000 nits of theinventive compounds Compound 453, 781, 699, 22, and 473 (InventiveDevice Examples 1, 2, 3, 4, and 5) were also more stable than that ofthe Comparative Compound 1 (Comparative example 1) (8.55, 9.09, 5.73,1.53, 1.54 vs. 1.00).

It is understood that the various embodiments described herein are byway of example only, and are not intended to limit the scope of theinvention. For example, many of the materials and structures describedherein may be substituted with other materials and structures withoutdeviating from the spirit of the invention. The present invention asclaimed may therefore include variations from the particular examplesand preferred embodiments described herein, as will be apparent to oneof skill in the art. It is understood that various theories as to whythe invention works are not intended to be limiting.

We claim:
 1. An organic light emitting device (OLED) comprising: ananode; a cathode; and an organic layer, disposed between the anode andthe cathode, comprising a compound having the formula ofM(L¹)_(x)(L²)_(y)(L³)_(z); wherein M is selected from the groupconsisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu; wherein L¹, L², and L³can be the same or different; wherein x is 1, 2, or 3; wherein y is 0,1, or 2; wherein z is 0, 1, or 2; wherein x+y+z is the oxidation stateof the metal M; wherein L¹, L², and L³ are each independently selectedfrom the group consisting of:

wherein R_(a), R_(b), R_(c), and R_(d) independently represent mono, di,tri, or tetra substitution, or no substitution; wherein R_(a), R_(b),R_(c), and R_(d) are independently selected from the group consisting ofhydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl,alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl,alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester,nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, andcombinations thereof; wherein two adjacent substituents of R_(a), R_(b),R_(c), and R_(d) are optionally joined to form a ring or form amultidentate ligand; wherein at least one of the R_(a), R_(b), R_(c),and R_(d) includes at least one R, wherein R is selected from the groupconsisting of partially fluorinated alkyl, partially fluorinatedcycloalkyl, and combinations thereof; wherein each of the at least one Ris directly bonded to an aromatic ring; wherein in each of the at leastone R, C having an F attached thereto is separated by at least onecarbon atom from the aromatic ring; and wherein when one of L¹, L², andL³ is

then at least one of the other L¹, L², and L³ is different.
 2. The OLEDof claim 1, wherein the first compound is capable of emitting light froma triplet excited state to a ground singlet state at room temperature.3. The OLED of claim 1, wherein the first compound is a metalcoordination complex having a metal-carbon bond.
 4. The OLED of claim 1,wherein C having an F attached thereto is separated by at least twocarbon atoms from the aromatic ring.
 5. The OLED of claim 1, wherein Chaving an F attached thereto is separated by at least three carbon atomsfrom the aromatic ring.
 6. The OLED of claim 1, wherein each of the atleast one R contains at least one CF₃ group.
 7. The OLED of claim 1,wherein the first compound has the formula of Ir(L¹)₂(L²), wherein L¹has the formula selected from the group consisting of:

and wherein L² has the formula:


8. The OLED of claim 7, wherein L² has the formula:

wherein R_(e), R_(f), R_(h), and R_(i) are independently selected fromgroup consisting of alkyl, cycloalkyl, aryl, and heteroaryl; wherein atleast one of R_(e), R_(f), R_(h), and R_(i) has at least two carbonatoms; wherein R_(g) is selected from group consisting of hydrogen,deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy,aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl,aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile,isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinationsthereof.
 9. The OLED of claim 1, wherein L¹ and L² are different andeach independently selected from the group consisting of:


10. The OLED of claim 1, wherein L¹ and L² are each independentlyselected from the group consisting of:


11. The OLED of claim 1, wherein the first compound has the formula ofPt(L¹)₂ or Pt(L¹)(L²).
 12. The OLED of claim 1, wherein at least one ofR_(a), R_(b), R_(c), and R_(d) includes an alkyl or cycloalkyl groupthat includes CD, CD₂, or CD₃, wherein D is deuterium.
 13. The OLED ofclaim 1, wherein L¹, L², and L³ are each independently selected from thegroup consisting of:

wherein in L_(A1), R = R^(A1), in L_(A2), R = R^(A2), in L_(A3), R =R^(A3), in L_(A4), R = R^(A4), in L_(A5), R = R^(A5), in L_(A6), R =R^(A6), in L_(A7), R = R^(A7), in L_(A8), R = R^(A8), in L_(A9), R =R^(A9), in L_(A10), R = R^(A10), in L_(A11), R = R^(A11), in L_(A12), R= R^(A12), in L_(A13), R = R^(A13), in L_(A14), R = R^(A14), in L_(A15),R = R^(A15), in L_(A16), R = R^(A16), in L_(A17), R = R^(A17), inL_(A18), R = R^(A18), in L_(A19), R = R^(A19), in L_(A20), R = R^(A20),in L_(A21), R = R^(A21), in L_(A22), R = R^(A22), in L_(A23), R =R^(A23), in L_(A24), R = R^(A24), in L_(A25), R = R^(A25), in L_(A26), R= R^(A26), in L_(A27), R = R^(A27), in L_(A28), R = R^(A28), in L_(A29),R = R^(A29), in L_(A30), R = R^(A30), in L_(A31), R = R^(A31), inL_(A32), R = R^(A32), in L_(A33), R = R^(A33), in L_(A34), R = R^(A34),in L_(A35), R = R^(A35), in L_(A36), R = R^(A36), in L_(A37), R =R^(A37), in L_(A38), R = R^(A38), in L_(A39), R = R^(A39), in L_(A40), R= R^(A40), and in L_(A41), R = R^(A41);

wherein in L_(A42), R = R^(A1), in L_(A43), R = R^(A2), in L_(A44), R =R^(A3), in L_(A45), R = R^(A4), in L_(A46), R = R^(A5), in L_(A47), R =R^(A6), in L_(A48), R = R^(A7), in L_(A49), R = R^(A8), in L_(A50), R =R^(A9), in L_(A51), R = R^(A10), in L_(A52), R = R^(A11), in L_(A53), R= R^(A12), in L_(A54), R = R^(A13), in L_(A55), R = R^(A14), in L_(A56),R = R^(A15), in L_(A57), R = R^(A16), in L_(A58), R = R^(A17), inL_(A59), R = R^(A18), in L_(A60), R = R^(A19), in L_(A61), R = R^(A20),in L_(A62), R = R^(A21), in L_(A63), R = R^(A22), in L_(A64), R =R^(A23), in L_(A65), R = R^(A24), in L_(A66), R = R^(A25), in L_(A67), R= R^(A26), in L_(A68), R = R^(A27), in L_(A69), R = R^(A28), in L_(A70),R = R^(A29), in L_(A71), R = R^(A30), in L_(A72), R = R^(A31), inL_(A73), R = R^(A32), in L_(A74), R = R^(A33), in L_(A75), R = R^(A34),in L_(A76), R = R^(A35), in L_(A77), R = R^(A36), in L_(A78), R =R^(A37), in L_(A79), R = R^(A38), in L_(A80), R = R^(A39), in L_(A81), R= R^(A40), and in L_(A82), R = R^(A41);

wherein in L_(A83), R = R^(A1), in L_(A84), R = R^(A2), in L_(A85), R =R^(A3), in L_(A86), R = R^(A4), in L_(A87), R = R^(A5), in L_(A88), R =R^(A6), in L_(A89), R = R^(A7), in L_(A90), R = R^(A8), in L_(A91), R =R^(A9), in L_(A92), R = R^(A10), in L_(A93), R = R^(A11), in L_(A94), R= R^(A12), in L_(A95), R = R^(A13), in L_(A96), R = R^(A14), in L_(A97),R = R^(A15), in L_(A98), R = R^(A16), in L_(A99), R = R^(A17), inL_(A100), R = R^(A18), in L_(A101), R = R^(A19), in L_(A102), R =R^(A20), in L_(A103), R = R^(A21), in L_(A104), R = R^(A22), inL_(A105), R = R^(A23), in L_(A106), R = R^(A24), in L_(A107), R =R^(A25), in L_(A108), R = R^(A26), in L_(A109), R = R^(A27), inL_(A110), R = R^(A28), in L_(A111), R = R^(A29), in L_(A112), R =R^(A30), in L_(A113), R = R^(A31), in L_(A114), R = R^(A32), inL_(A115), R = R^(A33), in L_(A116), R = R^(A34), in L_(A117), R =R^(A35), in L_(A118), R = R^(A36), in L_(A119), R = R^(A37), inL_(A120), R = R^(A38), in L_(A121), R = R^(A39), in L_(A122), R =R^(A40), and in L_(A123), R = R^(A41);

wherein in L_(A124), R = R^(A1), in L_(A125), R = R^(A2), in L_(A126), R= R^(A3), in L_(A127), R = R^(A4), in L_(A128), R = R^(A5), in L_(A129),R = R^(A6), in L_(A130), R = R^(A7), in L_(A131), R = R^(A8), inL_(A132), R = R^(A9), in L_(A133), R = R^(A10), in L_(A134), R =R^(A11), in L_(A135), R = R^(A12), in L_(A136), R = R^(A13), inL_(A137), R = R^(A14), in L_(A138), R = R^(A15), in L_(A139), R =R^(A16), in L_(A140), R = R^(A17), in L_(A141), R = R^(A18), inL_(A142), R = R^(A19), in L_(A143), R = R^(A20), in L_(A144), R =R^(A21), in L_(A145), R = R^(A22), in L_(A146), R = R^(A23), inL_(A147), R = R^(A24), in L_(A148), R = R^(A25), in L_(A149), R =R^(A26), in L_(A150), R = R^(A27), in L_(A151), R = R^(A28), inL_(A152), R = R^(A29), in L_(A153), R = R^(A30), in L_(A154), R =R^(A31), in L_(A155), R = R^(A32), in L_(A156), R = R^(A33), inL_(A157), R = R^(A34), in L_(A158), R = R^(A35), in L_(A159), R =R^(A36), in L_(A160), R = R^(A37), in L_(A161), R = R^(A38), inL_(A162), R = R^(A39), in L_(A163), R = R^(A40), and in L_(A164), R =R^(A41),

wherein in L_(A165), R = R^(A1), in L_(A166), R = R^(A2), in L_(A167), R= R^(A3), in L_(A168), R = R^(A4), in L_(A169), R = R^(A5), in L_(A170),R = R^(A6), in L_(A171), R = R^(A7), in L_(A172), R = R^(A8), inL_(A173), R = R^(A9), in L_(A174), R = R^(A10), in L_(A175), R =R^(A11), in L_(A176), R = R^(A12), in L_(A177), R = R^(A13), inL_(A178), R = R^(A14), in L_(A179), R = R^(A15), in L_(A180), R =R^(A16), in L_(A181), R = R^(A17), in L_(A182), R = R^(A18), inL_(A183), R = R^(A19), in L_(A184), R = R^(A20), in L_(A185), R =R^(A21), in L_(A186), R = R^(A22), in L_(A187), R = R^(A23), inL_(A188), R = R^(A24), in L_(A189), R = R^(A25), in L_(A190), R =R^(A26), in L_(A191), R = R^(A27), in L_(A192), R = R^(A28), inL_(A193), R = R^(A29), in L_(A194), R = R^(A30), in L_(A195), R =R^(A31), in L_(A196), R = R^(A32), in L_(A197), R = R^(A33), inL_(A198), R = R^(A34), in L_(A199), R = R^(A35), in L_(A200), R =R^(A36), in L_(A201), R = R^(A37), in L_(A202), R = R^(A38), inL_(A203), R = R^(A39), in L_(A204), R = R^(A40), and in L_(A205), R =R^(A41);

wherein in L_(A206), R = R^(A1), in L_(A207), R = R^(A2), in L_(A208), R= R^(A3), in L_(A209), R = R^(A4), in L_(A210), R = R^(A5), in L_(A211),R = R^(A6), in L_(A212), R = R^(A7), in L_(A213), R = R^(A8), inL_(A214), R = R^(A9), in L_(A215), R = R^(A10), in L_(A216), R =R^(A11), in L_(A217), R = R^(A12), in L_(A218), R = R^(A13), inL_(A219), R = R^(A14), in L_(A220), R = R^(A15), in L_(A221), R =R^(A16), in L_(A222), R = R^(A17), in L_(A223), R = R^(A18), inL_(A224), R = R^(A19), in L_(A225), R = R^(A20), in L_(A226), R =R^(A21), in L_(A227), R = R^(A22), in L_(A228), R = R^(A23), inL_(A229), R = R^(A24), in L_(A230), R = R^(A25), in L_(A231), R =R^(A26), in L_(A232), R = R^(A27), in L_(A233), R = R^(A28), inL_(A234), R = R^(A29), in L_(A235), R = R^(A30), in L_(A236), R =R^(A31), in L_(A237), R = R^(A32), in L_(A238), R = R^(A33), inL_(A239), R = R^(A34), in L_(A240), R = R^(A35), in L_(A241), R =R^(A36), in L_(A242), R = R^(A37), in L_(A243), R = R^(A38), inL_(A244), R = R^(A39), in L_(A245), R = R^(A40), and in L_(A246), R =R^(A41);

wherein in L_(A247), R = R^(A1), in L_(A248), R = R^(A2), in L_(A249), R= R^(A3), in L_(A250), R = R^(A4), in L_(A251), R = R^(A5), in L_(A252),R = R^(A6), in L_(A253), R = R^(A7), in L_(A254), R = R^(A8), inL_(A255), R = R^(A9), in L_(A256), R = R^(A10), in L_(A257), R =R^(A11), in L_(A258), R = R^(A12), in L_(A259), R = R^(A13), inL_(A260), R = R^(A14), in L_(A261), R = R^(A15), in L_(A262), R =R^(A16), in L_(A263), R = R^(A17), in L_(A264), R = R^(A18), inL_(A265), R = R^(A19), in L_(A266), R = R^(A20), in L_(A267), R =R^(A21), in L_(A268), R = R^(A22), in L_(A269), R = R^(A23), inL_(A270), R = R^(A24), in L_(A271), R = R^(A25), in L_(A272), R =R^(A26), in L_(A273), R = R^(A27), in L_(A274), R = R^(A28), inL_(A275), R = R^(A29), in L_(A276), R = R^(A30), in L_(A277), R =R^(A31), in L_(A278), R = R^(A32), in L_(A279), R = R^(A33), inL_(A280), R = R^(A34), in L_(A281), R = R^(A35), in L_(A282), R =R^(A36), in L_(A283), R = R^(A37), in L_(A284), R = R^(A38), inL_(A285), R = R^(A39), in L_(A286), R = R^(A40), and in L_(A287), R =R^(A41);

wherein in L_(A288), R = R^(A1), in L_(A289), R = R^(A2), in L_(A290), R= R^(A3), in L_(A291), R = R^(A4), in L_(A292), R = R^(A5), in L_(A293),R = R^(A6), in L_(A294), R = R^(A7), in L_(A295), R = R^(A8), inL_(A296), R = R^(A9), in L_(A297), R = R^(A10), in L_(A298), R =R^(A11), in L_(A299), R = R^(A12), in L_(A300), R = R^(A13), inL_(A301), R = R^(A14), in L_(A302), R = R^(A15), in L_(A303), R =R^(A16), in L_(A304), R = R^(A17), in L_(A305), R = R^(A18), inL_(A306), R = R^(A19), in L_(A307), R = R^(A20), in L_(A308), R =R^(A21), in L_(A309), R = R^(A22), in L_(A310), R = R^(A23), inL_(A311), R = R^(A24), in L_(A312), R = R^(A25), in L_(A313), R =R^(A26), in L_(A314), R = R^(A27), in L_(A315), R = R^(A28), inL_(A316), R = R^(A29), in L_(A317), R = R^(A30), in L_(A318), R =R^(A31), in L_(A319), R = R^(A32), in L_(A320), R = R^(A33), inL_(A321), R = R^(A34), in L_(A322), R = R^(A35), in L_(A323), R =R^(A36), in L_(A324), R = R^(A37), in L_(A325), R = R^(A38), inL_(A326), R = R^(A39), in L_(A327), R = R^(A40), and in L_(A328), R =R^(A41);

wherein in L_(A329), R = R^(A1), in L_(A330), R = R^(A2), in L_(A331), R= R^(A3), in L_(A332), R = R^(A4), in L_(A333), R = R^(A5), in L_(A334),R = R^(A6), in L_(A335), R = R^(A7), in L_(A336), R = R^(A8), inL_(A337), R = R^(A9), in L_(A338), R = R^(A10), in L_(A339), R =R^(A11), in L_(A340), R = R^(A12), in L_(A341), R = R^(A13), inL_(A342), R = R^(A14), in L_(A343), R = R^(A15), in L_(A344), R =R^(A16), in L_(A345), R = R^(A17), in L_(A346), R = R^(A18), inL_(A347), R = R^(A19), in L_(A348), R = R^(A20), in L_(A349), R =R^(A21), in L_(A350), R = R^(A22), in L_(A351), R = R^(A23), inL_(A352), R = R^(A24), in L_(A353), R = R^(A25), in L_(A354), R =R^(A26), in L_(A355), R = R^(A27), in L_(A356), R = R^(A28), inL_(A357), R = R^(A29), in L_(A358), R = R^(A30), in L_(A359), R =R^(A31), in L_(A360), R = R^(A32), in L_(A361), R = R^(A33), inL_(A362), R = R^(A34), in L_(A363), R = R^(A35), in L_(A364), R =R^(A36), in L_(A365), R = R^(A37), in L_(A366), R = R^(A38), inL_(A367), R = R^(A39), in L_(A368), R = R^(A40), and in L_(A369), R =R^(A41);

wherein in L_(A370), R = R^(A1), in L_(A371), R = R^(A2), in L_(A372), R= R^(A3), in L_(A373), R = R^(A4), in L_(A374), R = R^(A5), in L_(A375),R = R^(A6), in L_(A376), R = R^(A7), in L_(A377), R = R^(A8), inL_(A378), R = R^(A9), in L_(A379), R = R^(A10), in L_(A380), R =R^(A11), in L_(A381), R = R^(A12), in L_(A382), R = R^(A13), inL_(A383), R = R^(A14), in L_(A384), R = R^(A15), in L_(A385), R =R^(A16), in L_(A386), R = R^(A17), in L_(A387), R = R^(A18), inL_(A388), R = R^(A19), in L_(A389), R = R^(A20), in L_(A390), R =R^(A21), in L_(A391), R = R^(A22), in L_(A392), R = R^(A23), inL_(A393), R = R^(A24), in L_(A394), R = R^(A25), in L_(A395), R =R^(A26), in L_(A396), R = R^(A27), in L_(A397), R = R^(A28), inL_(A398), R = R^(A29), in L_(A399), R = R^(A30), in L_(A400), R =R^(A31), in L_(A401), R = R^(A32), in L_(A402), R = R^(A33), inL_(A403), R = R^(A34), in L_(A404), R = R^(A35), in L_(A405), R =R^(A36), in L_(A406), R = R^(A37), in L_(A407), R = R^(A38), inL_(A408), R = R^(A39), in L_(A409), R = R^(A40), and in L_(A410), R =R^(A41);

wherein in L_(A411), R = R^(A1), in L_(A412), R = R^(A2), in L_(A413), R= R^(A3), in L_(A414), R = R^(A4), in L_(A415), R = R^(A5), in L_(A416),R = R^(A6), in L_(A417), R = R^(A7), in L_(A418), R = R^(A8), inL_(A419), R = R^(A9), in L_(A420), R = R^(A10), in L_(A421), R =R^(A11), in L_(A422), R = R^(A12), in L_(A423), R = R^(A13), inL_(A424), R = R^(A14), in L_(A425), R = R^(A15), in L_(A426), R =R^(A16), in L_(A427), R = R^(A17), in L_(A428), R = R^(A18), inL_(A429), R = R^(A19), in L_(A430), R = R^(A20), in L_(A431), R =R^(A21), in L_(A432), R = R^(A22), in L_(A433), R = R^(A23), inL_(A434), R = R^(A24), in L_(A435), R = R^(A25), in L_(A436), R =R^(A26), in L_(A437), R = R^(A27), in L_(A438), R = R^(A28), inL_(A439), R = R^(A29), in L_(A440), R = R^(A30), in L_(A441), R =R^(A31), in L_(A442), R = R^(A32), in L_(A443), R = R^(A33), inL_(A444), R = R^(A34), in L_(A445), R = R^(A35), in L_(A446), R =R^(A36), in L_(A447), R = R^(A37), in L_(A448), R = R^(A38), inL_(A449), R = R^(A39), in L_(A450), R = R^(A40), and in L_(A451), R =R^(A41);

wherein, R^(A1) through R^(A41) have the formulas:


14. The OLED of claim 1, wherein the first compound has the formula ofIr(L¹)₂(L²), wherein L¹ is selected from the group consisting of

wherein in L_(A1), R = R^(A1), in L_(A2), R = R^(A2), in L_(A3), R =R^(A3), in L_(A4), R = R^(A4), in L_(A5), R = R^(A5), in L_(A6), R =R^(A6), in L_(A7), R = R^(A7), in L_(A8), R = R^(A8), in L_(A9), R =R^(A9), in L_(A10), R = R^(A10), in L_(A11), R = R^(A11), in L_(A12), R= R^(A12), in L_(A13), R = R^(A13), in L_(A14), R = R^(A14), in L_(A15),R = R^(A15), in L_(A16), R = R^(A16), in L_(A17), R = R^(A17), inL_(A18), R = R^(A18), in L_(A19), R = R^(A19), in L_(A20), R = R^(A20),in L_(A21), R = R^(A21), in L_(A22), R = R^(A22), in L_(A23), R =R^(A23), in L_(A24), R = R^(A24), in L_(A25), R = R^(A25), in L_(A26), R= R^(A26), in L_(A27), R = R^(A27), in L_(A28), R = R^(A28), in L_(A29),R = R^(A29), in L_(A30), R = R^(A30), in L_(A31), R = R^(A31), inL_(A32), R = R^(A32), in L_(A33), R = R^(A33), in L_(A34), R = R^(A34),in L_(A35), R = R^(A35), in L_(A36), R = R^(A36), in L_(A37), R =R^(A37), in L_(A38), R = R^(A38), in L_(A39), R = R^(A39), in L_(A40), R= R^(A40), and in L_(A41), R = R^(A41);

wherein in L_(A42), R = R^(A1), in L_(A43), R = R^(A2), in L_(A44), R =R^(A3), in L_(A45), R = R^(A4), in L_(A46), R = R^(A5), in L_(A47), R =R^(A6), in L_(A48), R = R^(A7), in L_(A49), R = R^(A8), in L_(A50), R =R^(A9), in L_(A51), R = R^(A10), in L_(A52), R = R^(A11), in L_(A53), R= R^(A12), in L_(A54), R = R^(A13), in L_(A55), R = R^(A14), in L_(A56),R = R^(A15), in L_(A57), R = R^(A16), in L_(A58), R = R^(A17), inL_(A59), R = R^(A18), in L_(A60), R = R^(A19), in L_(A61), R = R^(A20),in L_(A62), R = R^(A21), in L_(A63), R = R^(A22), in L_(A64), R =R^(A23), in L_(A65), R = R^(A24), in L_(A66), R = R^(A25), in L_(A67), R= R^(A26), in L_(A68), R = R^(A27), in L_(A69), R = R^(A28), in L_(A70),R = R^(A29), in L_(A71), R = R^(A30), in L_(A72), R = R^(A31), inL_(A73), R = R^(A32), in L_(A74), R = R^(A33), in L_(A75), R = R^(A34),in L_(A76), R = R^(A35), in L_(A77), R = R^(A36), in L_(A78), R =R^(A37), in L_(A79), R = R^(A38), in L_(A80), R = R^(A39), in L_(A81), R= R^(A40), and in L_(A82), R = R^(A41);

wherein in L_(A83), R = R^(A1), in L_(A84), R = R^(A2), in L_(A85), R =R^(A3), in L_(A86), R = R^(A4), in L_(A87), R = R^(A5), in L_(A88), R =R^(A6), in L_(A89), R = R^(A7), in L_(A90), R = R^(A8), in L_(A91), R =R^(A9), in L_(A92), R = R^(A10), in L_(A93), R = R^(A11), in L_(A94), R= R^(A12), in L_(A95), R = R^(A13), in L_(A96), R = R^(A14), in L_(A97),R = R^(A15), in L_(A98), R = R^(A16), in L_(A99), R = R^(A17), inL_(A100), R = R^(A18), in L_(A101), R = R^(A19), in L_(A102), R =R^(A20), in L_(A103), R = R^(A21), in L_(A104), R = R^(A22), inL_(A105), R = R^(A23), in L_(A106), R = R^(A24), in L_(A107), R =R^(A25), in L_(A108), R = R^(A26), in L_(A109), R = R^(A27), inL_(A110), R = R^(A28), in L_(A111), R = R^(A29), in L_(A112), R =R^(A30), in L_(A113), R = R^(A31), in L_(A114), R = R^(A32), inL_(A115), R = R^(A33), in L_(A116), R = R^(A34), in L_(A117), R =R^(A35), in L_(A118), R = R^(A36), in L_(A119), R = R^(A37), inL_(A120), R = R^(A38), in L_(A121), R = R^(A39), in L_(A122), R =R^(A40), and in L_(A123), R = R^(A41);

wherein in L_(A124), R = R^(A1), in L_(A125), R = R^(A2), in L_(A126), R= R^(A3), in L_(A127), R = R^(A4), in L_(A128), R = R^(A5), in L_(A129),R = R^(A6), in L_(A130), R = R^(A7), in L_(A131), R = R^(A8), inL_(A132), R = R^(A9), in L_(A133), R = R^(A10), in L_(A134), R =R^(A11), in L_(A135), R = R^(A12), in L_(A136), R = R^(A13), inL_(A137), R = R^(A14), in L_(A138), R = R^(A15), in L_(A139), R =R^(A16), in L_(A140), R = R^(A17), in L_(A141), R = R^(A18), inL_(A142), R = R^(A19), in L_(A143), R = R^(A20), in L_(A144), R =R^(A21), in L_(A145), R = R^(A22), in L_(A146), R = R^(A23), inL_(A147), R = R^(A24), in L_(A148), R = R^(A25), in L_(A149), R =R^(A26), in L_(A150), R = R^(A27), in L_(A151), R = R^(A28), inL_(A152), R = R^(A29), in L_(A153), R = R^(A30), in L_(A154), R =R^(A31), in L_(A155), R = R^(A32), in L_(A156), R = R^(A33), inL_(A157), R = R^(A34), in L_(A158), R = R^(A35), in L_(A159), R =R^(A36), in L_(A160), R = R^(A37), in L_(A161), R = R^(A38), inL_(A162), R = R^(A39), in L_(A163), R = R^(A40), and in L_(A164), R =R^(A41),

wherein in L_(A165), R = R^(A1), in L_(A166), R = R^(A2), in L_(A167), R= R^(A3), in L_(A168), R = R^(A4), in L_(A169), R = R^(A5), in L_(A170),R = R^(A6), in L_(A171), R = R^(A7), in L_(A172), R = R^(A8), inL_(A173), R = R^(A9), in L_(A174), R = R^(A10), in L_(A175), R =R^(A11), in L_(A176), R = R^(A12), in L_(A177), R = R^(A13), inL_(A178), R = R^(A14), in L_(A179), R = R^(A15), in L_(A180), R =R^(A16), in L_(A181), R = R^(A17), in L_(A182), R = R^(A18), inL_(A183), R = R^(A19), in L_(A184), R = R^(A20), in L_(A185), R =R^(A21), in L_(A186), R = R^(A22), in L_(A187), R = R^(A23), inL_(A188), R = R^(A24), in L_(A189), R = R^(A25), in L_(A190), R =R^(A26), in L_(A191), R = R^(A27), in L_(A192), R = R^(A28), inL_(A193), R = R^(A29), in L_(A194), R = R^(A30), in L_(A195), R =R^(A31), in L_(A196), R = R^(A32), in L_(A197), R = R^(A33), inL_(A198), R = R^(A34), in L_(A199), R = R^(A35), in L_(A200), R =R^(A36), in L_(A201), R = R^(A37), in L_(A202), R = R^(A38), inL_(A203), R = R^(A39), in L_(A204), R = R^(A40), and in L_(A205), R =R^(A41);

wherein in L_(A206), R = R^(A1), in L_(A207), R = R^(A2), in L_(A208), R= R^(A3), in L_(A209), R = R^(A4), in L_(A210), R = R^(A5), in L_(A211),R = R^(A6), in L_(A212), R = R^(A7), in L_(A213), R = R^(A8), inL_(A214), R = R^(A9), in L_(A215), R = R^(A10), in L_(A216), R =R^(A11), in L_(A217), R = R^(A12), in L_(A218), R = R^(A13), inL_(A219), R = R^(A14), in L_(A220), R = R^(A15), in L_(A221), R =R^(A16), in L_(A222), R = R^(A17), in L_(A223), R = R^(A18), inL_(A224), R = R^(A19), in L_(A225), R = R^(A20), in L_(A226), R =R^(A21), in L_(A227), R = R^(A22), in L_(A228), R = R^(A23), inL_(A229), R = R^(A24), in L_(A230), R = R^(A25), in L_(A231), R =R^(A26), in L_(A232), R = R^(A27), in L_(A233), R = R^(A28), inL_(A234), R = R^(A29), in L_(A235), R = R^(A30), in L_(A236), R =R^(A31), in L_(A237), R = R^(A32), in L_(A238), R = R^(A33), inL_(A239), R = R^(A34), in L_(A240), R = R^(A35), in L_(A241), R =R^(A36), in L_(A242), R = R^(A37), in L_(A243), R = R^(A38), inL_(A244), R = R^(A39), in L_(A245), R = R^(A40), and in L_(A246), R =R^(A41);

wherein in L_(A247), R = R^(A1), in L_(A248), R = R^(A2), in L_(A249), R= R^(A3), in L_(A250), R = R^(A4), in L_(A251), R = R^(A5), in L_(A252),R = R^(A6), in L_(A253), R = R^(A7), in L_(A254), R = R^(A8), inL_(A255), R = R^(A9), in L_(A256), R = R^(A10), in L_(A257), R =R^(A11), in L_(A258), R = R^(A12), in L_(A259), R = R^(A13), inL_(A260), R = R^(A14), in L_(A261), R = R^(A15), in L_(A262), R =R^(A16), in L_(A263), R = R^(A17), in L_(A264), R = R^(A18), inL_(A265), R = R^(A19), in L_(A266), R = R^(A20), in L_(A267), R =R^(A21), in L_(A268), R = R^(A22), in L_(A269), R = R^(A23), inL_(A270), R = R^(A24), in L_(A271), R = R^(A25), in L_(A272), R =R^(A26), in L_(A273), R = R^(A27), in L_(A274), R = R^(A28), inL_(A275), R = R^(A29), in L_(A276), R = R^(A30), in L_(A277), R =R^(A31), in L_(A278), R = R^(A32), in L_(A279), R = R^(A33), inL_(A280), R = R^(A34), in L_(A281), R = R^(A35), in L_(A282), R =R^(A36), in L_(A283), R = R^(A37), in L_(A284), R = R^(A38), inL_(A285), R = R^(A39), in L_(A286), R = R^(A40), and in L_(A287), R =R^(A41);

wherein in L_(A288), R = R^(A1), in L_(A289), R = R^(A2), in L_(A290), R= R^(A3), in L_(A291), R = R^(A4), in L_(A292), R = R^(A5), in L_(A293),R = R^(A6), in L_(A294), R = R^(A7), in L_(A295), R = R^(A8), inL_(A296), R = R^(A9), in L_(A297), R = R^(A10), in L_(A298), R =R^(A11), in L_(A299), R = R^(A12), in L_(A300), R = R^(A13), inL_(A301), R = R^(A14), in L_(A302), R = R^(A15), in L_(A303), R =R^(A16), in L_(A304), R = R^(A17), in L_(A305), R = R^(A18), inL_(A306), R = R^(A19), in L_(A307), R = R^(A20), in L_(A308), R =R^(A21), in L_(A309), R = R^(A22), in L_(A310), R = R^(A23), inL_(A311), R = R^(A24), in L_(A312), R = R^(A25), in L_(A313), R =R^(A26), in L_(A314), R = R^(A27), in L_(A315), R = R^(A28), inL_(A316), R = R^(A29), in L_(A317), R = R^(A30), in L_(A318), R =R^(A31), in L_(A319), R = R^(A32), in L_(A320), R = R^(A33), inL_(A321), R = R^(A34), in L_(A322), R = R^(A35), in L_(A323), R =R^(A36), in L_(A324), R = R^(A37), in L_(A325), R = R^(A38), inL_(A326), R = R^(A39), in L_(A327), R = R^(A40), and in L_(A328), R =R^(A41);

wherein in L_(A329), R = R^(A1), in L_(A330), R = R^(A2), in L_(A331), R= R^(A3), in L_(A332), R = R^(A4), in L_(A333), R = R^(A5), in L_(A334),R = R^(A6), in L_(A335), R = R^(A7), in L_(A336), R = R^(A8), inL_(A337), R = R^(A9), in L_(A338), R = R^(A10), in L_(A339), R =R^(A11), in L_(A340), R = R^(A12), in L_(A341), R = R^(A13), inL_(A342), R = R^(A14), in L_(A343), R = R^(A15), in L_(A344), R =R^(A16), in L_(A345), R = R^(A17), in L_(A346), R = R^(A18), inL_(A347), R = R^(A19), in L_(A348), R = R^(A20), in L_(A349), R =R^(A21), in L_(A350), R = R^(A22), in L_(A351), R = R^(A23), inL_(A352), R = R^(A24), in L_(A353), R = R^(A25), in L_(A354), R =R^(A26), in L_(A355), R = R^(A27), in L_(A356), R = R^(A28), inL_(A357), R = R^(A29), in L_(A358), R = R^(A30), in L_(A359), R =R^(A31), in L_(A360), R = R^(A32), in L_(A361), R = R^(A33), inL_(A362), R = R^(A34), in L_(A363), R = R^(A35), in L_(A364), R =R^(A36), in L_(A365), R = R^(A37), in L_(A366), R = R^(A38), inL_(A367), R = R^(A39), in L_(A368), R = R^(A40), and in L_(A369), R =R^(A41);

wherein in L_(A370), R = R^(A1), in L_(A371), R = R^(A2), in L_(A372), R= R^(A3), in L_(A373), R = R^(A4), in L_(A374), R = R^(A5), in L_(A375),R = R^(A6), in L_(A376), R = R^(A7), in L_(A377), R = R^(A8), inL_(A378), R = R^(A9), in L_(A379), R = R^(A10), in L_(A380), R =R^(A11), in L_(A381), R = R^(A12), in L_(A382), R = R^(A13), inL_(A383), R = R^(A14), in L_(A384), R = R^(A15), in L_(A385), R =R^(A16), in L_(A386), R = R^(A17), in L_(A387), R = R^(A18), inL_(A388), R = R^(A19), in L_(A389), R = R^(A20), in L_(A390), R =R^(A21), in L_(A391), R = R^(A22), in L_(A392), R = R^(A23), inL_(A393), R = R^(A24), in L_(A394), R = R^(A25), in L_(A395), R =R^(A26), in L_(A396), R = R^(A27), in L_(A397), R = R^(A28), inL_(A398), R = R^(A29), in L_(A399), R = R^(A30), in L_(A400), R =R^(A31), in L_(A401), R = R^(A32), in L_(A402), R = R^(A33), inL_(A403), R = R^(A34), in L_(A404), R = R^(A35), in L_(A405), R =R^(A36), in L_(A406), R = R^(A37), in L_(A407), R = R^(A38), inL_(A408), R = R^(A39), in L_(A409), R = R^(A40), and in L_(A410), R =R^(A41);

wherein in L_(A411), R = R^(A1), in L_(A412), R = R^(A2), in L_(A413), R= R^(A3), in L_(A414), R = R^(A4), in L_(A415), R = R^(A5), in L_(A416),R = R^(A6), in L_(A417), R = R^(A7), in L_(A418), R = R^(A8), inL_(A419), R = R^(A9), in L_(A420), R = R^(A10), in L_(A421), R =R^(A11), in L_(A422), R = R^(A12), in L_(A423), R = R^(A13), inL_(A424), R = R^(A14), in L_(A425), R = R^(A15), in L_(A426), R =R^(A16), in L_(A427), R = R^(A17), in L_(A428), R = R^(A18), inL_(A429), R = R^(A19), in L_(A430), R = R^(A20), in L_(A431), R =R^(A21), in L_(A432), R = R^(A22), in L_(A433), R = R^(A23), inL_(A434), R = R^(A24), in L_(A435), R = R^(A25), in L_(A436), R =R^(A26), in L_(A437), R = R^(A27), in L_(A438), R = R^(A28), inL_(A439), R = R^(A29), in L_(A440), R = R^(A30), in L_(A441), R =R^(A31), in L_(A442), R = R^(A32), in L_(A443), R = R^(A33), inL_(A444), R = R^(A34), in L_(A445), R = R^(A35), in L_(A446), R =R^(A36), in L_(A447), R = R^(A37), in L_(A448), R = R^(A38), inL_(A449), R = R^(A39), in L_(A450), R = R^(A40), and in L_(A451), R =R^(A41);

wherein, R^(A1) through R^(A41) have the formulas:

and wherein L² is selected from the group consisting of:


15. The OLED of claim 14, wherein the first compound is selected fromthe group consisting of Compound 1 through Compound 5,863; and whereineach of Compound x, where x=451j+k−451, k is an integer from 1 to 451,and j is an integer from 1 to 13, has the formula Ir(L_(Ak))₂(L_(Bj)).16. The OLED of claim 1, wherein the first compound is selected from thegroup consisting of


17. An emissive layer in an organic light emitting device, the emissivelayer comprising a compound having the formula ofM(L¹)_(x)(L²)_(y)(L³)_(z); wherein M is selected from the groupconsisting of Ir, R_(h), R_(e), Ru, Os, Pt, Au, and Cu; wherein L¹, L²,and L³ can be the same or different; wherein x is 1, 2, or 3; wherein yis 0, 1, or 2; wherein z is 0, 1, or 2; wherein x+y+z is the oxidationstate of the metal M; wherein L¹, L², and L³ are each independentlyselected from the group consisting of:

wherein R_(a), R_(b), R_(e), and R_(d) independently represent mono, di,tri, or tetra substitution, or no substitution; wherein R_(a), R_(b),R_(c), and R_(d) are independently selected from the group consisting ofhydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl,alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl,alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester,nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, andcombinations thereof; wherein two adjacent substituents of R_(a), R_(b),R_(e), and R_(d) are optionally joined to form a ring or form amultidentate ligand; wherein at least one of the R_(a), R_(b), R_(e),and R_(d) includes at least one R, wherein R is selected from the groupconsisting of partially fluorinated alkyl, partially fluorinatedcycloalkyl, and combinations thereof; wherein each of the at least one Ris directly bonded to an aromatic ring; wherein in each of the at leastone R, C having an F attached thereto is separated by at least onecarbon atom from the aromatic ring; and wherein when one of L¹, L², andL³ is

then at least one of the other L¹, L², and L³ is different.
 18. Theemissive layer of claim 17, wherein the compound is selected from thegroup consisting of


19. The emissive layer of claim 17, wherein the emissive layer furthercomprises a host, wherein the host comprises at least one selected fromthe group consisting of metal complex, triphenylene, carbazole,dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene,azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, andaza-dibenzoselenophene.
 20. A consumer product comprising an organiclight-emitting device comprising: an anode; a cathode; and an organiclayer, disposed between the anode and the cathode, comprising acompound, wherein the compound is selected from the group consisting of

wherein the consumer product is selected from the group consisting offlat panel displays, computer monitors, medical monitors, televisions,billboards, lights for interior or exterior illumination and/orsignaling, heads-up displays, fully or partially transparent displays,flexible displays, laser printers, telephones, cell phones, tablets,phablets, personal digital assistants (PDAs), laptop computers, digitalcameras, camcorders, viewfinders, micro-displays, 3-D displays,vehicles, a wall, theater or stadium screen, and a sign.